Yihang Li, Jenny Hui Foong Chau, Yan Wang, Chunli Xie, Jia Wang, Liangtao Xie, Wei Lu, Chao Zou, Yuliang Liu, Haoyu Li. “Transient polarity amplification enables Markovnikov hydroamination with free alkyl amines.” ChemRxiv (). https://doi.org/10.26434/chemrxiv.15007663/v1

Photoreaction quantum-yield results were not retained

α-methylstyrene
Identifier 1
Cyclic voltammetry, potential E₁/₂ = −2.60 V vs. SCE
Cyclic voltammetry, conditions CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆ in CH₃CN; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN
Main, p. 4; SI, p. S6
4-vinylanisole
Cyclic voltammetry, potential Eₚ/₂ = −2.81 V vs. SCE
Cyclic voltammetry, conditions CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆ in CH₃CN; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN
SI, p. S6
5,10-diphenyl-5,10-dihydrophenazine
Identifier PAZ
Cyclic voltammetry, ground-state redox oxidation potential +0.18 V vs SCE
Cyclic voltammetry, graphical potential annotations +0.23 V, +0.12 V, +1.08 V, +0.94 V vs SCE
Cyclic voltammetry, conditions Conditions stated for Figs. S3–S7: alkene substrates (5 mM) and n-Bu₄NPF₆ (0.1 M) in CH₃CN; CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN
Normalized absorption and emission spectra, intersection 417 nm (2.97 eV)
SI, pp. S6, S8–S9
PAZ and α-methylstyrene
α-Methylstyrene identifier 1
Stern–Volmer fluorescence quenching α-Methylstyrene quenched the excited state of PAZ; y = 0.0137x + 1, R² = 0.999
Stern–Volmer fluorescence quenching, conditions PAZ (0.5 mM) in CH₃CN in a 3.5 mL quartz cuvette; excitation at 365 nm; emission intensity at 465 nm; baseline and quencher concentrations of 12.5, 25, 37.5, 50, and 62.5 mM
EPR reported in Main (415 nm, 10 min) Clear EPR signal; isotropic g = 2.001; assigned to PAZ˙⁺
EPR reported in SI (415 nm, 5 min) No signal in the dark; after irradiation, g = 2.001 and AN = 0.632 mT; assigned to the PAZ radical cation
EPR reported in SI, sample 1 (0.4 mmol), PAZ (0.004 mmol), and CH₃CN (1.0 mL); 20 μL aliquot in a capillary tube inside an EPR tube
Main, p. 4; SI, pp. S9–S11
PAZ and n-butylamine
n-Butylamine identifier 2
Stern–Volmer fluorescence quenching No measurable quenching; y = −0.000113x + 1, R² = 0.999
Stern–Volmer fluorescence quenching, conditions PAZ (0.5 mM) in CH₃CN in a 3.5 mL quartz cuvette; excitation at 365 nm; emission intensity at 465 nm; baseline and quencher concentrations of 12.5, 25, 37.5, 50, and 62.5 mM
EPR reported in Main Irradiated PAZ and 2 remained EPR-silent
EPR reported in SI (415 nm irradiation) No EPR signal was observed
EPR reported in SI, sample CH₃CN solution (0.4 M) containing PAZ (0.004 mmol) and 2 (0.6 mmol)
Main, p. 4; SI, pp. S9–S11
methyl (S)-3-amino-4-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoate
Identifier s1
¹H NMR (500 MHz, CDCl₃) δ 7.80 (d, J = 8.0 Hz, 1H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.24 (t, J = 7.5 Hz, 1H), 7.15 (d, J = 7.5 Hz, 2H), 4.85 (ddd, J = 8.0, 6.5, 6.5 Hz, 1H), 3.72 (s, 3H), 3.70 – 3.66 (m, 1H), 3.69 (s, 3H), 3.15 (dd, J = 14.0, 6.0 Hz, 1H), 3.09 (dd, J = 14.0, 6.0 Hz, 1H), 2.84 (dd, J = 16.5, 3.5 Hz, 1H), 2.55 (dd, J = 12.0, 3.5 Hz, 1H)
¹³C NMR (125 MHz, CDCl₃) δ 172.9, 172.2, 171.8, 135.9, 129.2, 128.5, 127.0, 52.9, 52.2, 51.8, 51.8, 39.0, 38.0
SI, p. S17
methyl(4-(prop-1-en-2-yl)phenyl)sulfane
Identifier s2
¹H NMR (500 MHz, CDCl₃) δ 7.40 (d, J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 5.35 (s, 1H), 5.06 – 5.04 (m, 1H), 2.49 (s, 3H), 2.13 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 142.5, 138.0, 137.5, 126.4, 125.9, 111.9, 21.7, 15.9
SI, p. S18
1-(tert-butyl)-4-(prop-1-en-2-yl)benzene
Identifier s3
¹H NMR (500 MHz, CDCl₃) δ 7.42 (d, J = 8.5 Hz, 2H), 7.35 (d, J = 8.5 Hz, 2H), 5.35 (s, 1H), 5.05 – 5.02 (m, 1H), 2.14 (s, 3H), 1.32 (s, 9H)
¹³C NMR (125 MHz, CDCl₃) δ 150.4, 142.9, 138.3, 125.2, 125.1, 111.7, 34.5, 31.3, 21.8
SI, p. S18
4-(prop-1-en-2-yl)-1,1'-biphenyl
Identifier s4
¹H NMR (500 MHz, CDCl₃) δ 7.60 (d, J = 8.5 Hz, 2H), 7.58 – 7.54 (m, 4H), 7.44 (dd, J = 7.5, 7.5 Hz, 2H), 7.34 (t, J = 7.5 Hz, 1H), 5.43 (s, 1H), 5.11 (d, J = 1.5 Hz, 1H), 2.19 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 142.8, 140.8, 140.2, 140.1, 128.8, 127.3, 127.0, 126.9, 125.9, 112.5, 21.8
SI, pp. S18–S19
4,4,5,5-tetramethyl-2-(4-(prop-1-en-2-yl)phenyl)-1,3,2-dioxaborolane
Identifier s5
¹H NMR (500 MHz, CDCl₃) δ 7.77 (d, J = 8.0 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 5.41 (s, 1H), 5.12 (s, 1H), 2.16 (s, 3H), 1.35 (s, 12H)
¹³C NMR (125 MHz, CDCl₃) δ 144.0, 143.3, 134.7, 124.8, 113.2, 83.7, 24.8, 21.7
¹³C NMR reporting qualifier The boron-bound carbon was not detected
SI, p. S19
5-(prop-1-en-2-yl)benzo[d][1,3]dioxole
Identifier s6
Cyclic voltammetry, potential Eₚ/₂ = −2.94 V vs. SCE
Cyclic voltammetry, conditions CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; CH₃CN; Fc internal reference, E(Fc⁺/Fc) = 380 mV in CH₃CN
¹H NMR (500 MHz, CDCl₃) δ 6.98 (d, J = 1.5 Hz, 1H), 6.94 (dd, J = 8.0, 1.5 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 5.94 (s, 2H), 5.22 (s, 1H), 5.00 – 4.97 (m, 1H), 2.10 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 147.6, 147.0, 142.7, 135.6, 119.1, 111.3, 107.9, 106.0, 101.0, 22.1
SI, pp. S6–S7, S19–S20
1,3-dimethoxy-5-(prop-1-en-2-yl)benzene
Identifier s7
¹H NMR (500 MHz, CDCl₃) δ 6.61 (d, J = 2.0 Hz, 2H), 6.40 (t, J = 2.0 Hz, 1H), 5.35 (s, 1H), 5.08 (s, 1H), 3.80 (s, 6H), 2.12 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 160.6, 143.5, 143.3, 112.8, 104.0, 99.3, 55.3, 21.9
SI, p. S20
N,N-dimethyl-4-(prop-1-en-2-yl)aniline
Identifier s8
Cyclic voltammetry, potential Eₚ/₂ = −2.93 V vs. SCE
Cyclic voltammetry, conditions CHI760E potentiostat; glassy carbon working electrode; platinum-wire counter electrode; Ag/AgNO₃ reference electrode; 5 mM substrate and 0.1 M n-Bu₄NPF₆; 100 mV s⁻¹; N₂ atmosphere; sparged with N₂ for at least 15 min; DMSO; Fc internal reference, E(Fc⁺/Fc) = 435 mV in DMSO
¹H NMR (500 MHz, CDCl₃) δ 7.39 (d, J = 9.0 Hz, 2H), 6.70 (d, J = 9.0 Hz, 2H), 5.25 (s, 1H), 4.91 – 4.89 (m, 1H), 2.95 (s, 6H), 2.12 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 150.0, 142.7, 129.3, 126.2, 112.1, 108.8, 40.6, 21.8
SI, pp. S6–S7, S20
2-(prop-1-en-2-yl)benzofuran
Identifier s9
¹H NMR (500 MHz, CDCl₃) δ 7.53 (d, J = 7.5 Hz, 1H), 7.44 (dd, J = 8.5, 1.0 Hz, 1H), 7.26 (ddd, J = 7.0, 7.0, 1.0 Hz, 2H), 7.19(td, J = 7.0, 7.0, 1.0 Hz, 1H), 6.64 (s, 1H), 5.79 (s, 1H), 5.19 – 5.16 (m, 1H), 2.13 (dd, J = 1.5, 1.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 156.9, 154.8, 132.8, 129.0, 124.5, 122.6, 120.9, 113.2, 111.0, 102.8, 19.4
SI, pp. S20–S21
2-methoxy-5-(prop-1-en-2-yl)pyridine
Identifier s10
¹H NMR (500 MHz, CDCl₃) δ 8.25 (d, J = 2.5 Hz, 1H), 7.69 (dd, J = 8.5, 2.5 Hz, 1H), 6.71 (d, J = 8.5 Hz, 1H), 5.30 (s, 1H), 5.07 – 5.01 (m, 1H), 3.94 (s, 3H), 2.13 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 163.5, 143.8, 140.1, 135.8, 129.9, 111.8, 110.3, 53.4, 21.6
SI, p. S21
methyl 4-(1-(4-methoxyphenyl)vinyl)benzoate
Identifier s11
¹H NMR (500 MHz, CDCl₃) δ 8.00 (d, J = 8.5 Hz, 2H), 7.41 (d, J = 8.5 Hz, 2H), 7.24 (d, J = 8.5 Hz, 2H), 6.87 (d, J = 8.5 Hz, 2H), 5.48 (s, 1H), 5.43 (s, 1H), 3.93 (s, 3H), 3.83 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 167.0, 159.5, 148.7, 146.4, 133.3, 129.5, 129.3, 129.3, 128.3, 114.5, 113.7, 55.3, 52.1
SI, pp. S21–S22
2-(1-phenylvinyl)thiophene
Identifier s12
¹H NMR (500 MHz, CDCl₃) δ 7.46 – 7.41 (m, 2H), 7.39 – 7.33 (m, 3H), 7.23 (dd, J = 5.5, 1.0 Hz, 1H), 6.98 (dd, J = 5.5, 3.5 Hz, 1H), 6.91 (dd, J = 3.5, 1.0 Hz, 1H), 5.58 (d, J = 1.0 Hz, 1H), 5.24 (d, J = 1.0 Hz, 1H)
¹³C NMR (125 MHz, CDCl₃) δ 144.8, 143.4, 141.0, 128.3, 128.2, 128.0, 127.3, 126.5, 125.0, 113.6
SI, p. S22
5-methylene-10,11-dihydro-5H-dibenzo[a,d][7]annulene
Identifier s13
¹H NMR (500 MHz, CDCl₃) δ 7.34 (d, J = 7.5 Hz, 2H), 7.21 – 7.15 (m, 4H), 7.11 (d, J = 7.5 Hz, 2H), 5.42 – 5.40 (m, 2H), 3.14 (s, 4H)
¹³C NMR (125 MHz, CDCl₃) δ 151.9, 141.2, 138.4, 128.9, 128.2, 127.7, 126.2, 117.5, 33.3
SI, p. S22
1-methylene-1,2,3,4-tetrahydronaphthalene
Identifier s14
¹H NMR (500 MHz, CDCl₃) δ 7.65 (d, J = 7.0 Hz, 1H), 7.19 – 7.13 (m, 2H), 7.10 (d, J = 7.0 Hz, 1H), 5.48 (s, 1H), 4.96 (s, 1H), 2.85 (t, J = 6.5 Hz, 2H), 2.55 (t, J = 6.5 Hz, 2H), 1.92 – 1.85 (m, 2H)
¹³C NMR (125 MHz, CDCl₃) δ 143.4, 137.3, 134.7, 129.2, 127.6, 125.9, 124.2, 107.8, 33.2, 30.4, 23.8
SI, p. S23
hex-1-en-2-ylbenzene
Identifier s15
¹H NMR (500 MHz, CDCl₃) δ 7.41 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.26 (t, J = 7.5 Hz, 1H), 5.26 (s, 1H), 5.05 (s, 1H), 2.50 (t, J = 7.5 Hz, 2H), 1.47 – 1.39 (m, 2H), 1.39 – 1.30 (m, 2H), 0.89 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 148.7, 141.4, 128.2, 127.2, 126.1, 112.0, 35.0, 30.4, 22.4, 13.9
SI, p. S23
(1-cyclopropylvinyl)benzene
Identifier s16
¹H NMR (500 MHz, CDCl₃) δ 7.59 (d, J = 7.0 Hz, 2H), 7.34 (dd, J = 7.0, 7.0 Hz, 2H), 7.28 (t, J = 7.0 Hz, 1H), 5.27 (s, 1H), 4.93 (s, 1H), 1.68 – 1.62 (m, 1H), 0.86 – 0.82 (m, 2H), 0.61 – 0.58 (m, 2H)
¹³C NMR (125 MHz, CDCl₃) δ 149.4, 141.6, 128.1, 127.4, 126.1, 109.0, 15.6, 6.7
SI, pp. S23–S24
(1-cyclohexylvinyl)benzene
Identifier s17
¹H NMR (500 MHz, CDCl₃) δ 7.34 – 7.23 (m, 5H), 5.13 (d, J = 1.5 Hz, 1H), 5.00 (dd, J = 1.5, 1.5 Hz, 1H), 2.42 (tt, J = 11.5, 3.0 Hz, 1H), 1.87 – 1.81 (m, 2H), 1.78 (dt, J = 13.0, 3.5 Hz, 2H), 1.73 – 1.68 (m, 1H), 1.37 – 1.27 (m, 2H), 1.23 – 1.10 (m, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 155.0, 143.0, 128.1, 127.0, 126.6, 110.3, 42.6, 32.7, 26.8, 26.4
SI, p. S24
1-methoxy-4-(3-methylbut-3-en-1-yn-1-yl)benzene
Identifier s18
¹H NMR (500 MHz, CDCl₃) δ 7.38 (d, J = 9.0 Hz, 2H), 6.84 (d, J = 9.0 Hz, 2H), 5.37 – 5.34 (m, 1H), 5.27 – 5.25 (m, 1H), 3.82 (s, 3H), 1.98 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 159.4, 133.0, 127.0, 121.2, 115.3, 113.9, 89.2, 88.3, 55.2, 23.6
SI, pp. S24–S25
(8R,9S,13S,14S)-13-methyl-3-(prop-1-en-2-yl)-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one
Identifier s19
¹H NMR (500 MHz, CDCl₃) δ 7.29 – 7.26 (m, 2H), 7.20 (s, 1H), 5.33 (s, 1H), 5.04 (s, 1H), 2.93 (dd, J = 9.0, 4.0 Hz, 2H), 2.51 (dd, J = 19.0, 8.5 Hz, 1H), 2.46 – 2.41 (m, 1H), 2.31 (ddd, J = 10.5, 10.5, 3.5 Hz, 1H), 2.19 – 2.10 (m, 1H), 2.13 (s, 3H), 2.10 – 2.00 (m, 2H), 1.99 – 1.94 (m, 2H), 1.68 – 1.41 (m, 6H), 0.91 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 221.0, 142.9, 139.0, 138.7, 136.2, 126.1, 125.2, 122.9, 111.8, 50.4, 47.9, 44.3, 38.1, 35.8, 31.5, 29.5, 26.5, 25.6, 21.8, 21.5, 13.8
SI, p. S25
ethyl (E)-3-(3,4-dimethoxyphenyl)acrylate
Identifier s20
¹H NMR (500 MHz, CDCl₃) δ 7.63 (d, J = 16.0 Hz, 1H), 7.11 (dd, J = 8.0, 2.0 Hz, 1H), 7.06 (d, J = 2.0 Hz, 1H), 6.87 (d, J = 8.0 Hz, 1H), 6.31 (d, J = 16.0 Hz, 1H), 4.26 (q, J = 7.0 Hz, 2H), 3.92 (s, 3H), 3.92 (s, 3H), 1.34 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 167.2, 151.1, 149.2, 144.5, 127.5, 122.6, 116.0, 111.0, 109.6, 60.4, 56.0, 55.9, 14.4
SI, pp. S25–S26
N-(1-(4-iodo-2,6-dimethylphenoxy)propan-2-yl)acetamide
Identifier s21
¹H NMR (500 MHz, CDCl₃) δ 7.34 (s, 2H), 5.82 (d, J = 7.5 Hz, 1H), 4.38 – 4.30 (m, 1H), 3.77 (dd, J = 9.0, 4.0 Hz, 1H), 3.67 (dd, J = 9.0, 3.0 Hz, 1H), 2.21 (s, 6H), 2.02 (s, 3H), 1.39 (d, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 169.4, 154.9, 137.6, 133.3, 87.9, 73.9, 45.3, 23.4, 17.6, 15.7
HRMS (ESI) m/z calcd for C₁₃H₁₉NIO₂ [M + H]⁺ 348.0455; found 348.0453
IR (ATR) νmax 3278, 3101, 2970, 1647, 1562, 1471, 1372, 1202, 869 cm⁻¹
SI, pp. S26–S27
N-(1-(2,6-dimethyl-4-(prop-1-en-2-yl)phenoxy)propan-2-yl)acetamide
Identifier s22
¹H NMR (500 MHz, CDCl₃) δ 7.12 (s, 2H), 5.94 (br s, 1H), 5.28 (s, 1H), 5.01 (s, 1H), 4.39 – 4.30 (m, 1H), 3.80 (dd, J = 9.0, 4.0 Hz, 1H), 3.70 (dd, J = 9.0, 3.0 Hz, 1H), 2.26 (s, 6H), 2.11 (s, 3H), 2.04 (s, 3H), 1.41 (d, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 169.4, 154.3, 142.7, 137.0, 130.3, 126.2, 111.7, 73.9, 45.3, 23.5, 21.9, 17.7, 16.3
HRMS (ESI) m/z calcd for C₁₆H₂₄NO₂ [M + H]⁺ 262.1802; found 262.1801
IR (ATR) νmax 3273, 3089, 2987, 1648, 1611, 1472, 1367, 1196, 762 cm⁻¹
SI, pp. S26–S27
methyl 2-(3-(1-phenylvinyl)phenyl)propanoate
Identifier s23
¹H NMR (500 MHz, CDCl₃) δ 7.35 – 7.31 (m, 5H), 7.30 – 7.24 (m, 3H), 7.22 (ddd, J = 7.0, 1.5, 1.5 Hz, 1H), 5.47 (s, 1H), 5.46 (s, 1H), 3.71 (q, J = 7.0 Hz, 1H), 3.66 (s, 3H), 1.49 (d, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 174.9, 149.8, 141.8, 141.3, 140.5, 128.4, 128.2, 128.2, 127.8, 127.5, 127.2, 126.7, 114.5, 52.0, 45.3, 18.6
SI, pp. S27–S28
methyl 5-(2,5-dimethyl-4-vinylphenoxy)-2,2-dimethylpentanoate
Identifier s24
¹H NMR (500 MHz, CDCl₃) δ 7.27 (s, 1H), 6.85 (dd, J = 16.5, 11.0 Hz, 1H), 6.55 (s, 1H), 5.52 (d, J = 16.5 Hz, 1H), 5.14 (d, J = 11.0 Hz, 1H), 3.92 (t, J = 5.5 Hz, 2H), 3.66 (s, 3H), 2.31 (s, 3H), 2.19 (s, 3H), 1.77 – 1.68 (m, 4H), 1.22 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 178.2, 156.6, 134.2, 133.9, 128.5, 127.5, 124.3, 112.7, 112.5, 68.0, 51.7, 42.0, 37.0, 25.1, 25.1, 19.6, 15.7
HRMS (ESI) m/z calcd for C₁₈H₂₇O₃ [M + H]⁺ 291.1955; found 291.1954
IR (ATR) νmax 3086, 2973, 1724, 1609. 1504, 1396, 1260, 1194, 899 cm⁻¹
SI, p. S28
N-(2-phenylpropan-2-yl)butan-1-amine
Identifier 3
¹H NMR (500 MHz, CDCl₃) δ 7.42 (dd, J = 8.5, 1.5 Hz, 2H), 7.33 (dd, J = 8.5, 8.5 Hz, 2H), 7.21 (tt, J = 8.5, 1.5 Hz, 1H), 2.30 (t, J = 7.0 Hz, 2H), 1.49 (br s, 1H), 1.45 (s, 6H), 1.43 – 1.36 (m, 2H), 1.33 – 1.24 (m, 2H), 0.85 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 148.0, 128.1, 126.1, 125.6, 55.7, 42.7, 33.1, 29.6, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₃H₂₂N [M + H]⁺ 192.1747; found 192.1746
IR (ATR) νmax 3322, 3085, 2958, 1601, 1494, 1378, 1181, 763, 698 cm⁻¹
SI, pp. S29–S30
N-benzyl-2-phenylpropan-1-d-2-amine-d
Identifier 4
¹H NMR (500 MHz, DMSO-d₆) δ 7.54 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.31 – 7.25 (m, 4H), 7.22 – 7.16 (m, 2H), 3.35 (s, 2H), 1.43 (s, 3H), 1.42 – 1.37 (m, 2H)
¹³C NMR (125 MHz, DMSO-d₆) δ 148.2, 141.7, 128.03, 127.99, 127.86, 126.3, 126.0, 125.8, 55.7 (t, JC-D = 7.5 Hz), 47.9, 29.5, 29.1 (t, JC-D = 18.8 Hz)
HRMS (ESI) m/z calcd for C₁₆H₁₈D₂N [M + H]⁺ 228.1716; found 228.1715
IR (ATR) νmax 3326, 3084, 2967, 2050, 1600, 1493, 1379, 1182, 763, 697 cm⁻¹
Deuterium labeling, D/H at the newly formed C–H bond >95 %
Deuterium labeling, conditions 1 (0.4 mmol), BnND₂ (1.5 equiv), PAZ (1 mol%), CH₃CN, 415 nm LEDs, 12 h
Main, p. 4; SI, p. S30
N-benzyl-2-phenylpropan-2-amine
Identifier 5
¹H NMR (500 MHz, CDCl₃) δ 7.53 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.32 – 7.27 (m, 4H), 7.26 – 7.19 (m, 2H), 3.48 (s, 2H), 1.57 (br s, 1H), 1.53 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.7, 141.2, 128.3, 128.2, 128.2, 126.7, 126.3, 125.9, 56.1, 47.6, 29.7
HRMS (ESI) m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1590
IR (ATR) νmax 3326, 3085, 2670, 1600, 1494, 1379, 1183, 763, 697 cm⁻¹
SI, pp. S30–S31
N-(cyclopropylmethyl)-2-phenylpropan-2-amine
Identifier 6
¹H NMR (500 MHz, CDCl₃) δ 7.42 (d, J = 8.0 Hz, 2H), 7.32 (dd, J = 8.0, 8.0 Hz, 2H), 7.21 (t, J = 8.0 Hz, 1H), 2.15 (d, J = 7.0 Hz, 2H), 1.59 (br s, 1H), 1.47 (s, 6H), 0.95 – 0.84 (m, 1H), 0.45 – 0.40 (m, 2H), 0.01 – -0.03 (m, 2H)
¹³C NMR (125 MHz, CDCl₃) δ 147.7, 128.1, 126.1, 125.6, 55.5, 48.3, 29.5, 11.7, 3.3
HRMS (ESI) m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1589
IR (ATR) νmax 3327, 3081, 2957, 1600, 1491, 1376, 1143, 762, 700 cm⁻¹
SI, p. S31
N-(cyclopentylmethyl)-2-phenylpropan-2-amine
Identifier 7
¹H NMR (500 MHz, CDCl₃) δ 7.43 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 2.24 (d, J = 7.0 Hz, 2H), 1.95 – 1.85 (m, 1H), 1.79 – 1.69 (m, 2H), 1.56 – 1.46 (m, 4H), 1.45 (s, 6H), 1.11 – 1.01 (m, 2H)
¹³C NMR (125 MHz, CDCl₃) δ 148.1, 128.1, 126.0, 125.8, 55.6, 48.7, 40.7, 30.9, 29.6, 25.2
HRMS (ESI) m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1903
IR (ATR) νmax 3326, 3085, 2864, 1601, 1494, 1378, 1182, 763, 698 cm⁻¹
SI, pp. S31–S32
N-(2-methoxyethyl)-2-phenylpropan-2-amine
Identifier 8
¹H NMR (500 MHz, CDCl₃) δ 7.44 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 3.45 (t, J = 5.5 Hz, 2H), 3.32 (s, 3H), 2.50 (t, J = 5.5 Hz, 2H), 1.81 (br s, 1H), 1.47 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.6, 128.1, 126.1, 125.7, 72.7, 58.6, 55.5, 42.4, 29.6
HRMS (ESI) m/z calcd for C₁₂H₂₀NO [M + H]⁺ 194.1540; found 194.1539
IR (ATR) νmax 3330, 3077, 2972, 1602, 1494, 1377, 1235, 1180, 763, 698 cm⁻¹
SI, p. S32
N-(2,2-diethoxyethyl)-2-phenylpropan-2-amine
Identifier 9
¹H NMR (500 MHz, CDCl₃) δ 7.44 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 4.54 (t, J = 5.5 Hz, 1H), 3.62 (dq, J = 9.5, 7.0 Hz, 2H), 3.48 (dq, J = 9.5, 7.0 Hz, 2H), 2.48 (d, J = 5.5 Hz, 2H), 1.66 (br s, 1H), 1.46 (s, 6H), 1.19 (t, J = 7.5 Hz, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.6, 128.1, 126.1, 125.7, 102.8, 62.1, 55.3, 45.6, 29.5, 15.3
HRMS (ESI) m/z calcd for C₁₅H₂₆NO₂ [M + H]⁺ 252.1958; found 252.1956
IR (ATR) νmax 3332, 3086, 2928, 1601, 1494, 1378, 1180, 1061, 764, 699 cm⁻¹
SI, p. S32
2-phenyl-N-(2,2,2-trifluoroethyl)propan-2-amine
Identifier 10
¹H NMR (500 MHz, CDCl₃) δ 7.45 (d, J = 7.5 Hz, 2H), 7.35 (dd, J = 7.5, 7.5 Hz, 2H), 7.24 (t, J = 7.5 Hz, 1H), 2.92 – 2.83 (m, 2H), 1.56 (br s, 1H), 1.48 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 146.3, 128.4, 126.7, 125.8, 125.7 (q, JC-F = 272.5 Hz), 55.8, 45.3 (q, JC-F = 31.3 Hz), 29.6
¹⁹F NMR (470 MHz, CDCl₃) δ −72.2 (t, JH-F = 9.4 Hz)
HRMS (ESI) m/z calcd for C₁₁H₁₅NF₃ [M + H]⁺ 218.1151; found 218.1151
IR (ATR) νmax 3350, 3089, 2971, 1602, 1496, 1267, 1186, 765, 699 cm⁻¹
SI, p. S33
3-((2-phenylpropan-2-yl)amino)propanenitrile
Identifier 11
¹H NMR (500 MHz, CDCl₃) δ 7.46 (d, J = 7.5 Hz, 2H), 7.34 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 2.62 (t, J = 6.5 Hz, 2H), 2.40 (t, J = 6.5 Hz, 2H), 1.57 (br s, 1H), 1.48 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 146.9, 128.3, 126.5, 125.7, 118.9, 56.0, 39.0, 29.6, 19.7
HRMS (ESI) m/z calcd for C₁₂H₁₇N₂ [M + H]⁺ 189.1386; found 189.1386
IR (ATR) νmax 3321, 3086, 2971, 2248, 1601, 1495, 1372, 1183, 766, 701 cm⁻¹
SI, p. S33
N-(2-(methylsulfonyl)ethyl)-2-phenylpropan-2-amine
Identifier 12
¹H NMR (500 MHz, CDCl₃) δ 7.44 (dd, J = 7.5, 1.0 Hz, 2H), 7.35 (dd, J = 7.5, 7.5 Hz, 2H), 7.24 (t, J = 7.5 Hz, 1H), 3.12 (t, J = 6.0 Hz, 2H), 2.94 (s, 3H), 2.85 (t, J = 6.0 Hz, 2H), 1.94 (br s, 1H), 1.50 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 146.4, 128.4, 126.7, 125.7, 56.4, 55.7, 42.0, 37.1, 29.1
HRMS (ESI) m/z calcd for C₁₂H₂₀NO₂S [M + H]⁺ 242.1209; found 242.1209
IR (ATR) νmax 3377, 3015, 2928, 1600, 1270, 1116, 764, 703 cm⁻¹
SI, p. S34
N-(2-phenylpropan-2-yl)pentan-3-amine
Identifier 13
¹H NMR (500 MHz, CDCl₃) δ 7.49 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5, 1H), 2.28 (p, J = 6.0 Hz, 1H), 1.47 (s, 6H), 1.28 – 1.20 (m, 4H), 0.74 (t, J = 7.5 Hz, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 148.9, 127.8, 126.1, 126.0, 55.6, 54.4, 29.9, 27.9, 9.8
HRMS (ESI) m/z calcd for C₁₄H₂₄N [M + H]⁺ 206.1903; found 206.1903
IR (ATR) νmax 3349, 3086, 2962, 1601, 1493, 1379, 1177, 762, 698 cm⁻¹
SI, p. S34
N-(2-phenylpropan-2-yl)cyclobutanamine
Identifier 14
¹H NMR (500 MHz, CDCl₃) δ 7.44 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 3.09 – 3.02 (m, 1H), 2.08 – 1.99 (m, 2H), 1.71 – 1.60 (m, 2H), 1.59 – 1.49 (m, 2H), 1.42 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 148.4, 128.0, 126.1, 125.8, 56.0, 49.8, 34.2, 30.3, 15.1
HRMS (ESI) m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1590
IR (ATR) νmax 3321, 3085, 2963, 1601, 1494, 1378, 1183, 763, 698 cm⁻¹
SI, p. S35
N-(2-phenylpropan-2-yl)cyclopentanamine
Identifier 15
¹H NMR (500 MHz, CDCl₃) δ 7.44 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5 Hz, 2H), 7.21 (dd, J = 7.5 Hz, 1H), 2.79 – 2.72 (m, 2H), 1.73 – 1.67 (m, 2H), 1.64 – 1.56 (m, 2H), 1.45 (s, 6H), 1.41 – 1.32 (m, 2H), 1.26 – 1.16 (m, 2H)
¹³C NMR (125 MHz, CDCl₃) δ 148.9, 128.0, 126.1, 125.8, 56.2, 55.3, 35.7, 30.5, 23.9
HRMS (ESI) m/z calcd for C₁₄H₂₂N [M + H]⁺ 204.1747; found 204.1747
IR (ATR) νmax 3325, 3085, 2955, 1601, 1494, 1373, 1182, 764, 699 cm⁻¹
SI, p. S35
N-(2-phenylpropan-2-yl)cyclohexanamine
Identifier 16
¹H NMR (500 MHz, CDCl₃) δ 7.46 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 2.25 – 2.18 (m, 1H), 1.64 – 1.55 (m, 4H), 1.64 – 1.55 (m, 1H), 1.46 (s, 6H), 1.15 – 0.96 (m, 5H)
¹³C NMR (125 MHz, CDCl₃) δ 148.9, 127.8, 126.0, 125.9, 56.0, 52.0, 36.4, 30.4, 25.7, 25.5
HRMS (ESI) m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1903
IR (ATR) νmax 3329, 3086, 2923, 1601, 1494, 1378, 1180, 763, 698 cm⁻¹
SI, pp. S35–S36
N-(2-phenylpropan-2-yl)tetrahydro-2H-pyran-4-amine
Identifier 17
¹H NMR (500 MHz, CDCl₃) δ 7.47 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 3.81 (dt, J = 11.5, 3.0 Hz, 2H), 3.23 (td, J = 11.5, 2.0 Hz, 2H), 2.48 (tt, J = 10.5, 4.5 Hz, 1H), 1.54 – 1.48 (m, 3H), 1.47 (s, 6H), 1.41 – 1.32 (m, 2H)
¹³C NMR (125 MHz, CDCl₃) δ 148.6, 128.0, 126.3, 125.9, 67.1, 56.0, 49.3, 36.4, 30.5
HRMS (ESI) m/z calcd for C₁₄H₂₂NO [M + H]⁺ 220.1696; found 220.1695
IR (ATR) νmax 3308, 3086, 2938, 1601, 1494, 1379, 1235, 1168, 771 cm⁻¹
Single-crystal XRD, identification code z2
Single-crystal XRD, empirical formula C₁₄H₂₁NO
Single-crystal XRD, formula weight 219.32
Single-crystal XRD, temperature/K 100.0
Single-crystal XRD, crystal system monoclinic
Single-crystal XRD, space group P2₁
Single-crystal XRD, a/Å 7.4671(5)
Single-crystal XRD, b/Å 11.8631(9)
Single-crystal XRD, c/Å 7.7175(5)
Single-crystal XRD, α/° 90
Single-crystal XRD, β/° 112.218(3)
Single-crystal XRD, γ/° 90
Single-crystal XRD, volume/ų 632.88(8)
Single-crystal XRD, Z 2
Single-crystal XRD, ρcalc g/cm³ 1.151
Single-crystal XRD, μ/mm⁻¹ 0.071
Single-crystal XRD, F(000) 240.0
Single-crystal XRD, crystal size/mm³ 0.21 × 0.19 × 0.17
Single-crystal XRD, radiation MoKα (λ = 0.71073)
Single-crystal XRD, 2Θ range for data collection/° 5.702 to 55.118
Single-crystal XRD, index ranges −9 ≤ h ≤ 9, −15 ≤ k ≤ 15, −10 ≤ l ≤ 10
Single-crystal XRD, reflections collected 18121
Single-crystal XRD, independent reflections 2896 [Rint = 0.0870, Rsigma = 0.0552]
Single-crystal XRD, data/restraints/parameters 2896/3/152
Single-crystal XRD, goodness-of-fit on F² 1.072
Single-crystal XRD, final R indexes [I ≥ 2σ(I)] R1 = 0.0399, wR2 = 0.0834
Single-crystal XRD, final R indexes [all data] R1 = 0.0507, wR2 = 0.0928
Single-crystal XRD, largest diff. peak/hole / e Å⁻³ 0.15/−0.17
Single-crystal XRD, Flack parameter −0.5(19)
Single-crystal XRD, CCDC deposition number 2577572
SI, pp. S36, S38
N-(tert-butyl)-2-phenylpropan-2-amine
Identifier 18
¹H NMR (500 MHz, CDCl₃) δ 7.51 (d, J = 7.5 Hz, 2H), 7.27 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 1.54 (br s, 1H), 1.51 (s, 6H), 0.96 (s, 9H)
¹³C NMR (125 MHz, CDCl₃) δ 151.1, 127.6, 125.8, 125.7, 55.5, 51.8, 32.8, 32.6
HRMS (ESI) m/z calcd for C₁₃H₂₂N [M + H]⁺ 192.1747; found 192.1746
IR (ATR) νmax 3346, 3085, 2968, 1601, 1493, 1376, 1181, 764, 698 cm⁻¹
SI, p. S39
(3s,5s,7s)-N-(2-phenylpropan-2-yl)adamantan-1-amine
Identifier 19
¹H NMR (500 MHz, CDCl₃) δ 7.52 (d, J = 7.5 Hz, 2H), 7.27 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 1.90 – 1.85 (m, 3H), 1.61 (br s, 1H), 1.54 – 1.44 (m, 12H), 1.52 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 151.4, 127.6, 125.8, 125.7, 55.4, 52.6, 45.7, 36.5, 33.4, 29.9
HRMS (ESI) m/z calcd for C₁₉H₂₈N [M + H]⁺ 270.2216; found 270.2215
IR (ATR) νmax 3338, 3083, 2898, 1600, 1493, 1379, 1184, 771, 703 cm⁻¹
SI, p. S39
N-benzyl-N-methyl-2-phenylpropan-2-amine
Identifier 20
¹H NMR (500 MHz, CDCl₃) δ 7.69 (d, J = 8.0 Hz, 2H), 7.33 (dd, J = 8.0, 8.0 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 7.28 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 7.19 (t, J = 8.0 Hz, 1H), 3.39 (s, 2H), 2.12 (s, 3H), 1.44 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.7, 141.2, 128.3, 128.1, 128.0, 126.4, 126.2, 126.2, 60.3, 55.7, 34.5, 24.0
HRMS (ESI) m/z calcd for C₁₇H₂₂N [M + H]⁺ 240.1747; found 240.1747
IR (ATR) νmax 3086, 2904, 1602, 1493, 1178, 764, 698 cm⁻¹
SI, p. S40
N-methyl-N-(2-phenylpropan-2-yl)prop-2-en-1-amine
Identifier 21
¹H NMR (500 MHz, CDCl₃) δ 7.55 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5, 1H), 5.76 (ddt, J = 16.5, 10.0, 6.0 Hz, 1H), 5.11 (d, J = 16.5 Hz, 1H), 5.02 (d, J = 10.0 Hz, 1H), 2.83 (d, J = 6.0 Hz, 2H), 2.21 (s, 3H), 1.35 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.7, 137.9, 127.9, 126.1, 126.0, 115.7, 60.2, 54.8, 34.3, 24.0
HRMS (ESI) m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1590
IR (ATR) νmax 3083, 2972, 1642, 1600, 1492, 1377, 1181, 913, 764, 698 cm⁻¹
SI, p. S40
N-methyl-N-(2-phenylpropan-2-yl)prop-2-yn-1-amine
Identifier 22
¹H NMR (500 MHz, CDCl₃) δ 7.53 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 3.15 (d, J = 2.5 Hz, 2H), 2.40 (s, 3H), 2.16 (t, J = 2.5 Hz, 1H), 1.39 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 148.7, 128.1, 126.4, 126.0, 82.5, 71.4, 60.3, 41.0, 34.9, 24.2
HRMS (ESI) m/z calcd for C₁₃H₁₈N [M + H]⁺ 188.1434; found 188.1433
IR (ATR) νmax 3303, 3087, 2972, 1600, 1494, 1376, 1181, 759, 699 cm⁻¹
SI, p. S41
N,N-dibutyl-1-(4-methoxyphenyl)ethan-1-amine
Identifier 23
¹H NMR (500 MHz, CDCl₃) δ 7.26 (d, J = 8.0 Hz, 2H), 6.84 (d, J = 8.0 Hz, 2H), 3.80 (s, 3H), 3.79 (q, J = 7.0 Hz, 1H), 2.46 – 2.38 (m, 2H), 2.36 – 2.28 (m, 2H), 1.43 – 1.33 (m, 4H), 1.29 (d, J = 7.0 Hz, 3H), 1.27 – 1.20 (m, 4H), 0.86 (t, J = 7.5 Hz, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 158.1, 136.9, 128.7, 113.2, 58.1, 55.2, 49.5, 30.0, 20.6, 16.5, 14.1
HRMS (ESI) m/z calcd for C₁₄H₃₀NO [M + H]⁺ 264.2322; found 264.2322
IR (ATR) νmax 3061, 2955, 1610, 1509, 1376, 1243, 1174, 831 cm⁻¹
SI, p. S41
1-(2-phenylpropan-2-yl)azetidine
Identifier 24
¹H NMR (500 MHz, CDCl₃) δ 7.49 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.26 (t, J = 7.5 Hz, 1H), 3.28 (t, J = 6.5 Hz, 4H), 2.02 – 1.93 (m, 2H), 1.43 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 128.2, 127.0, 126.6 (Overlapped with 2C), 58.4, 47.4, 23.3, 15.7
HRMS (ESI) m/z calcd for C₁₂H₁₈N [M + H]⁺ 176.1434; found 176.1433
IR (ATR) νmax 3087, 2966, 1599, 1493, 1377, 1180, 793, 699 cm⁻¹
SI, p. S42
1-(2-phenylpropan-2-yl)pyrrolidine
Identifier 25
¹H NMR (500 MHz, CDCl₃) δ 7.51 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 2.55 – 2.49 (m, 4H), 1.72 – 1.67 (m, 4H), 1.42 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.9, 127.8, 126.3, 126.0, 57.5, 46.1, 24.6, 23.8
HRMS (ESI) m/z calcd for C₁₃H₂₀N [M + H]⁺ 190.1590; found 190.1591
IR (ATR) νmax 3083, 2968, 1599, 1491, 1379, 1178, 763, 698 cm⁻¹
SI, p. S42
2-phenyl-1-(2-phenylpropan-2-yl)pyrrolidine
Identifier 26
¹H NMR (500 MHz, CDCl₃) δ 7.56 (d, J = 7.5 Hz, 2H), 7.49 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 7.17 (t, J = 7.5 Hz, 1H), 4.22 (dd, J = 9.0, 3.5 Hz, 1H), 2.82 (ddd, J = 9.0, 6.5, 3.5 Hz, 1H), 2.59 (ddd, J = 9.0, 9.0, 6.5 Hz, 1H), 2.17 – 2.07 (m, 1H), 1.81 – 1.74 (m, 1H), 1.66 – 1.56 (m, 2H), 1.44 (s, 3H), 1.11 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 150.7, 149.5, 127.9, 127.8, 126.4, 126.4, 125.9, 125.8, 61.2, 59.5, 49.6, 37.7, 31.9, 24.5, 19.1
HRMS (ESI) m/z calcd for C₁₉H₂₄N [M + H]⁺ 266.1903; found 266.1902
IR (ATR) νmax 3083, 2967, 1600, 1490, 1381, 1185, 764, 697 cm⁻¹
SI, pp. S42–S43
tert-butyl (S)-(5-(2-phenylpropan-2-yl)-5-azaspiro[2.4]heptan-7-yl)carbamate
Identifier 27
¹H NMR (500 MHz, CDCl₃) δ 7.51 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 4.92 (br s, 1H), 3.71 – 3.63 (m, 1H), 2.96 – 2.88 (m, 1H), 2.62 (d, J = 8.0 Hz, 1H), 2.60 – 2.50 (m, 1H), 2.41 (d, J = 8.0 Hz, 1H), 1.43 (s, 9H), 1.39 (s, 3H), 1.38 (s, 3H), 0.77 – 0.67 (m, 2H), 0.54 – 0.48 (m, 1H), 0.43 – 0.37 (m, 1H)
¹³C NMR (125 MHz, CDCl₃) δ 155.7, 147.6, 127.9, 126.3, 126.0, 79.0, 57.3, 56.0, 54.2, 54.1, 31.7, 28.4, 26.3, 24.3, 24.2, 14.2, 8.3
HRMS (ESI) m/z calcd for C₂₀H₃₁N₂O₂ [M + H]⁺ 331.2380; found 331.2378
IR (ATR) νmax 3349, 3059, 2075, 1702, 1492, 1390, 1164, 765, 700 cm⁻¹
SI, p. S43
4-chloro-1-(2-phenylpropan-2-yl)piperidine
Identifier 28
¹H NMR (500 MHz, CDCl₃) δ 7.52 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 3.99 (m, 1H), 2.80 – 2.72 (m, 2H), 2.29 – 2.21 (m, 2H), 2.08 – 2.01 (m, 2H), 1.89 – 1.81 (m, 2H), 1.33 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.5, 128.0, 126.1, 125.8, 59.9, 58.6, 44.6, 36.7, 24.3
HRMS (ESI) m/z calcd for C₁₄H₂₁NCl [M + H]⁺ 238.1357; found 238.1357
IR (ATR) νmax 3084, 2968, 1598, 1491, 1376, 1174, 764, 699 cm⁻¹
SI, p. S44
4-fluoro-1-(2-phenylpropan-2-yl)piperidine
Identifier 29
¹H NMR (500 MHz, CDCl₃) δ 7.53 (d, J = 8.0, 2H), 7.30 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 4.68 – 4.56 (m, 1H), 2.67 – 2.62 (m, 2H), 2.37 – 2.33 (m, 2H), 1.92 – 1.75 (m, 4H), 1.34 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.6, 128.0, 126.1, 125.8, 89.7(d, JC-F = 170.0 Hz), 59.9, 42.6 (d, JC-F = 6.3 Hz), 32.6 (d, JC-F = 18.8 Hz), 24.3
¹⁹F NMR (470 MHz, CDCl₃) δ −178.5
HRMS (ESI) m/z calcd for C₁₄H₂₁NF [M + H]⁺ 222.1653; found 222.1652
IR (ATR) νmax 3085, 2971, 1601, 1492, 1367, 1178, 1029, 762, 699 cm⁻¹
SI, p. S44
4-(2-phenylpropan-2-yl)morpholine
Identifier 30
¹H NMR (500 MHz, CDCl₃) δ 7.53 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 4.5 Hz, 1H), 3.67 (t, J = 7.5 Hz, 4H), 2.47 (t, J = 7.5 Hz, 4H), 1.34 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 148.7, 128.0, 126.20, 126.19, 67.9, 59.6, 46.6, 23.8
HRMS (ESI) m/z calcd for C₁₃H₂₀NO [M + H]⁺ 206.1540; found 206.1538
IR (ATR) νmax 3063, 2851, 1610, 1510, 1371, 1240, 1177, 1116, 738 cm⁻¹
SI, p. S45
4-(2-phenylpropan-2-yl)thiomorpholine
Identifier 31
¹H NMR (500 MHz, CDCl₃) δ 7.50 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 2.77 – 2.75 (m, 4H), 2.64 – 2.62 (m, 4H), 1.32 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.5, 128.0, 126.1, 126.0, 60.8, 49.0, 29.0, 24.3
HRMS (ESI) m/z calcd for C₁₃H₂₀NS [M + H]⁺ 222.1311; found 222.1312
IR (ATR) νmax 3084, 2972, 1598, 1491, 1372, 1171, 732, 699 cm⁻¹
SI, p. S45
2-(2-phenylpropan-2-yl)-1,2,3,4-tetrahydroisoquinoline
Identifier 32
¹H NMR (500 MHz, CDCl₃) δ 7.60 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (t, J = 7.5 Hz, 1H), 7.12 – 7.07 (m, 3H), 7.03 – 7.00 (m, 1H), 3.81 (s, 2H), 2.77 (t, J = 5.5 Hz, 2H), 2.61 (t, J = 5.5 Hz, 2H), 1.44 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.4, 136.2, 135.3, 128.7, 128.0, 126.8, 126.2, 126.0, 125.7, 125.3, 60.0, 48.6, 44.8, 30.4, 23.9
HRMS (ESI) m/z calcd for C₁₈H₂₂N [M + H]⁺ 252.1747; found 252.1747
IR (ATR) νmax 3084, 2973, 1600, 1492, 1372, 1236, 741, 700 cm⁻¹
SI, pp. S45–S46
7-(1-(4-methoxyphenyl)ethyl)-2-oxa-7-azaspiro[3.5]nonane
Identifier 33
¹H NMR (500 MHz, CDCl₃) δ 7.19 (d, J = 8.5 Hz, 2H), 6.84 (d, J = 8.5 Hz, 2H), 4.35 (s, 4H), 3.80 (s, 3H), 3.33 (q, J = 6.5 Hz, 1H), 2.42 – 2.15 (m, 4H), 1.88 – 1.75 (m, 4H), 1.33 (d, J = 6.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.4, 135.6, 128.6, 113.4, 82.0, 63.9, 55.2, 47.4, 38.7, 35.2, 19.3
HRMS (ESI) m/z calcd for C₁₆H₂₄NO₂ [M + H]⁺ 262.1802; found 262.1802
IR (ATR) νmax 3061, 2925, 1610, 1510, 1372, 1243, 1177, 832, 741 cm⁻¹
SI, p. S46
1-(1-(4-methoxyphenyl)ethyl)azepane
Identifier 34
¹H NMR (500 MHz, CDCl₃) δ 7.30 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 3.79 (q, J = 6.5 Hz, 1H), 2.72 – 2.62 (m, 4H), 1.65 – 1.55 (m, 8H), 1.40 (d, J = 6.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.4, 128.8, 113.4 (overlapped with 2C), 62.9, 55.2, 51.9, 28.2, 27.0, 18.0
HRMS (ESI) m/z calcd for C₁₅H₂₄NO [M + H]⁺ 234.1853; found 234.1852
IR (ATR) νmax 3061, 2965, 1610, 1509, 1366, 1241, 1175, 732, 698 cm⁻¹
SI, pp. S46–S47
8-(1-(4-methoxyphenyl)ethyl)-3-oxa-8-azabicyclo[3.2.1]octane
Identifier 35
¹H NMR (500 MHz, CDCl₃) δ 7.28 (d, J = 9.0 Hz, 2H), 6.85 (d, J = 9.0 Hz, 2H), 3.81 – 3.75 (m, 1H), 3.80 (s, 3H), 3.61 (d, J = 10.0 Hz, 1H), 3.57 (dd, J = 10.0, 2.0 Hz, 1H), 3.40 – 3.33 (m, 2H), 3.29 (q, J = 6.5 Hz, 1H), 2.80 (d, J = 5.0 Hz, 1H), 2.00 – 1.68 (m, 4H), 1.25 (d, J = 6.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.5, 137.5, 128.4, 113.6, 73.5, 73.3, 58.7, 58.2, 57.6, 55.2, 25.1, 24.7, 22.0
HRMS (ESI) m/z calcd for C₁₅H₂₂NO₂ [M + H]⁺ 248.1645; found 248.1645
IR (ATR) νmax 3059, 2947, 1610, 1510, 1365, 1241, 1172, 831, 769 cm⁻¹
SI, pp. S47–S48
4-methoxy-N-(2-phenylpropan-2-yl)aniline
Identifier 36
¹H NMR (500 MHz, CDCl₃) δ 7.52 (dd, J = 7.5, 1.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.25 (t, J = 7.5 Hz, 1H), 6.61 (d, J = 9.0 Hz, 2H), 6.30 (d, J = 9.0 Hz, 2H), 3.67 (s, 3H), 1.60 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 152.0, 147.8, 140.1, 128.4, 126.2, 125.7, 117.1, 114.3, 56.0, 55.6, 30.6
HRMS (ESI) m/z calcd for C₁₆H₂₀NO [M + H]⁺ 242.1540; found 2442.1539
IR (ATR) νmax 3402, 3077, 2989, 1601, 1507, 1379, 1244, 1179, 777, 710 cm⁻¹
SI, p. S48
4-methyl-N-(2-phenylpropan-2-yl)aniline
Identifier 37
¹H NMR (500 MHz, CDCl₃) δ 7.51 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (t, J = 7.5 Hz, 1H), 6.82 (d, J = 8.0 Hz, 2H), 6.26 (d, J = 8.0 Hz, 2H), 3.90 (br s, 1H), 2.16 (s, 3H), 1.62 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.7, 143.7, 129.2, 128.5, 126.3, 126.2, 125.6, 115.5, 55.7, 30.7, 20.3
HRMS (ESI) m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1590
IR (ATR) νmax 3410, 3049, 2977, 1615, 1513, 1382, 1183, 760, 699 cm⁻¹
SI, p. S48
N-(2-phenylpropan-2-yl)aniline
Identifier 38
¹H NMR (500 MHz, CDCl₃) δ 7.51 (dd, J = 8.0, 1.5 Hz, 2H), 7.33 (dd, J = 8.0 Hz, 2H), 7.23 (t, J = 8.0 Hz, 1H), 7.00 (dd, J = 8.5, 7.5 Hz, 2H), 6.60 (t, J = 7.5 Hz, 1H), 6.33 (dd, J = 8.5, 1.5 Hz, 2H), 4.04 (br s, 1H), 1.64 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.4, 146.1, 128.7, 128.5, 126.3, 125.6, 117.0, 115.3, 55.7, 30.7
HRMS (ESI) m/z calcd for C₁₅H₁₈N [M + H]⁺ 212.1434; found 212.1434
IR (ATR) νmax 3419, 3082, 2978, 1599, 1490, 1378, 1176, 761, 701 cm⁻¹
SI, p. S49
4-chloro-N-(2-phenylpropan-2-yl)aniline
Identifier 39
¹H NMR (500 MHz, CDCl₃) δ 7.47 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 6.93 (d, J = 8.5 Hz, 2H), 6.24 (d, J = 8.5 Hz, 2H), 4.06 (br s, 1H), 1.62 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 146.9, 144.6, 128.6, 128.5, 126.5, 125.5, 121.7, 116.2, 55.9, 30.5
HRMS (ESI) m/z calcd for C₁₅H₁₇NCl [M + H]⁺ 246.1044; found 246.1042
IR (ATR) νmax 3414, 3085, 2978, 1595, 1490, 1380, 1178, 765, 695 cm⁻¹
SI, p. S49
4-((2-phenylpropan-2-yl)amino)benzonitrile
Identifier 40
¹H NMR (500 MHz, CDCl₃) δ 7.42 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.5, 7.5 Hz, 2H), 7.25 (t, J = 7.5 Hz, 1H), 7.23 (d, J = 8.5 Hz, 2H), 6.29 (d, J = 8.5 Hz, 2H), 4.66 (br s, 1H), 1.67 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.3, 145.7, 133.1, 128.8, 126.8, 125.2, 120.4, 114.5, 98.5, 56.1, 30.4
HRMS (ESI) m/z calcd for C₁₆H₁₇N₂ [M + H]⁺ 237.1386; found 237.1387
IR (ATR) νmax 3367, 3059, 2979, 2210, 1604, 1517, 1365, 1172, 766, 700 cm⁻¹
SI, p. S50
N-(2-phenylpropan-2-yl)naphthalen-2-amine
Identifier 41
¹H NMR (500 MHz, CDCl₃) δ 7.59 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.53 (dd, J = 8.0, 8.0 Hz, 2H), 7.35 – 7.31 (m, 3H), 7.24 (dd, J = 8.0, 8.0 Hz, 2H), 7.11 (t, J = 8.0 Hz, 1H), 6.75 (dd, J = 8.5, 2.0 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 4.23 (br s, 1H), 1.70 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.0, 143.5, 134.6, 128.6, 128.4, 127.4, 127.1, 126.4, 126.0, 125.9, 125.6, 121.9, 119.2, 108.3, 56.0, 30.6
HRMS (ESI) m/z calcd for C₁₉H₂₀N [M + H]⁺ 262.1590; found 262.1589
IR (ATR) νmax 3412, 3081, 2969, 1600, 1519, 1380, 1188, 748, 698 cm⁻¹
SI, p. S50
N-(2-phenylpropan-2-yl)pyridin-2-amine
Identifier 42
¹H NMR (500 MHz, CDCl₃) δ 8.04 (d, J = 4.0 Hz, 1H), 7.49 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.18 – 7.13 (m, 1H), 6.50 (dd, J = 7.0, 5.0 Hz, 1H), 5.82 (d, J = 7.5 Hz, 1H), 5.18 (br s, 1H), 1.68 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 157.4, 148.3, 146.7, 136.7, 128.6, 126.5, 125.4, 112.9, 108.0, 55.2, 30.4
HRMS (ESI) m/z calcd for C₁₄H₁₇N₂ [M + H]⁺ 213.1386; found 213.1386
IR (ATR) νmax 3278, 3081, 2975, 1600, 1576, 1442, 1382, 1193, 765, 701 cm⁻¹
SI, p. S51
N-phenyl-N-(2-phenylpropan-2-yl)aniline
Identifier 43
¹H NMR (500 MHz, CDCl₃) δ 7.61 (d, J = 8.5 Hz, 2H), 7.34 (t, J = 8.0 Hz, 2H), 7.23 – 7.20 (m, 1H), 7.19 – 7.15 (m, 4H), 6.93 (t, J = 7.0 Hz, 2H), 6.79 (d, J = 8.0 Hz, 4H), 1.56 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.0, 146.7, 128.8, 128.6, 126.1, 125.2, 124.7, 121.6, 61.3, 30.0
HRMS (ESI) m/z calcd for C₂₁H₂₂N [M + H]⁺ 288.1747; found 288.1750
IR (ATR) νmax 3069, 2992, 1586, 1487, 1386, 1172, 751, 702 cm⁻¹
SI, p. S51
N-methyl-N-(2-phenylpropan-2-yl)aniline
Identifier 44
¹H NMR (500 MHz, CDCl₃) δ 7.53 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.19 (dd, J = 7.5, 7.5 Hz, 2H), 7.02 (d, J = 7.5 Hz, 2H), 6.96 (t, J = 7.5 Hz, 1H), 2.70 (s, 3H), 1.46 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 150.2, 148.9, 128.1, 127.9, 126.2, 126.1, 125.2, 122.1, 60.9, 36.8, 27.1
HRMS (ESI) m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1591
IR (ATR) νmax 3084, 2975, 1596, 1490, 1380, 1179, 752, 698 cm⁻¹
SI, p. S52
1-(2-phenylpropan-2-yl)indoline
Identifier 45
¹H NMR (500 MHz, CDCl₃) δ 7.56 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.03 (d, J = 7.5 Hz, 1H), 6.88 (dd, J = 7.5, 7.5 Hz, 1H), 6.53 (dd, J = 7.5, 7.5 Hz, 1H), 5.63 (d, J = 7.5 Hz, 1H), 3.58 (t, J = 7.5 Hz, 2H), 2.99 (t, J = 7.5 Hz, 2H), 1.52 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 150.0, 148.6, 131.3, 128.5 (overlapped with 2C), 126.3, 125.4, 124.0, 116.9, 111.2, 58.5, 48.8, 28.2, 25.6
HRMS (ESI) m/z calcd for C₁₇H₂₀N [M + H]⁺ 238.1590; found 238.1592
IR (ATR) νmax 3058, 2973, 1604, 1483, 1382, 1191, 744, 698 cm⁻¹
SI, p. S52
9-(2-phenylpropan-2-yl)-9H-carbazole
Identifier 46
¹H NMR (500 MHz, CDCl₃) δ 8.09 (d, J = 7.5 Hz, 2H), 7.35 – 7.27 (m, 6H), 7.26 – 7.20 (m, 3H), 7.16 (dd, J = 7.5, 7.5 Hz, 2H), 2.24 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 148.6, 140.9, 128.8, 126.8, 125.1, 124.9, 124.4, 119.8, 118.7, 113.7, 64.1, 31.2
HRMS (ESI) m/z calcd for C₂₁H₂₀N [M + H]⁺ 286.1590; found 286.1590
IR (ATR) νmax 3059, 2980, 1592, 1493, 1387, 1179, 744, 696 cm⁻¹
SI, p. S53
10-(2-phenylpropan-2-yl)-10H-phenoxazine
Identifier 47
¹H NMR (500 MHz, CDCl₃) δ 7.50 (d, J = 7.5 Hz, 2H), 7.34 (dd, J = 7.5, 7.5 Hz, 2H), 7.28 (t, J = 7.5 Hz, 1H), 6.99 – 6.93 (m, 4H), 6.81 (td, J = 7.0, 2.0 Hz, 2H), 6.68 – 6.64 (m, 2H), 1.56 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 154.4, 147.6, 135.0, 128.0, 127.0, 126.8, 126.3, 124.5, 122.6, 116.2, 65.3, 28.6
HRMS (ESI) m/z calcd for C₂₁H₂₀NO [M + H]⁺ 302.1540; found 302.1538
IR (ATR) νmax 3058, 2987, 1489, 1382, 1263, 1182, 758, 700 cm⁻¹
SI, p. S53
10-(2-phenylpropan-2-yl)-10H-phenothiazine
Identifier 48
¹H NMR (500 MHz, CDCl₃) δ 7.62 (d, J = 7.5 Hz, 2H), 7.39 (dd, J = 7.5, 7.5 Hz, 2H), 7.27 (t, J = 7.5 Hz, 1H), 7.23 – 7.20 (m, 2H), 7.03 – 6.97 (m, 4H), 6.97 – 6.92 (m, 2H), 1.75 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 148.7, 145.5, 132.9, 128.2, 127.5, 126.9, 126.4, 126.0, 124.6, 123.5, 64.9, 32.3
HRMS (ESI) m/z calcd for C₂₁H₂₀NS [M + H]⁺ 318.1311; found 318.1312
IR (ATR) νmax 3057, 2979, 1589, 1492, 1389, 1174, 751, 705 cm⁻¹
SI, p. S54
1-(2-phenylpropan-2-yl)-1H-imidazole
Identifier 49
¹H NMR (500 MHz, CDCl₃) δ 7.63 (s, 1H), 7.31 (dd, J = 7.0, 7.0 Hz, 2H), 7.27 (t, J = 7.0, 1H), 7.09 (s, 1H), 7.06 (d, J = 7.0 Hz, 2H), 6.91 (s, 1H), 1.92 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 146.0, 135.6, 129.2, 128.6, 127.5, 124.8, 117.8, 60.0, 30.4
HRMS (ESI) m/z calcd for C₁₂H₁₅N₂ [M + H]⁺ 187.1230; found 187.1229
IR (ATR) νmax 3123, 3088, 2984, 1491, 1373, 1230, 1189, 770, 701, 663 cm⁻¹
SI, p. S54
1-(2-phenylpropan-2-yl)-1H-pyrazole
Identifier 50
¹H NMR (500 MHz, CDCl₃) δ 7.58 (d, J = 2.0 Hz, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.03 – 7.00 (m, 2H), 6.29 (dd, J = 2.0, 2.0 Hz, 1H), 1.98 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 146.8, 138.8, 128.4, 127.6, 127.1, 124.9, 105.2, 63.5, 29.8
HRMS (ESI) m/z calcd for C₁₂H₁₅N₂ [M + H]⁺ 187.1230; found 187.1230
IR (ATR) νmax 3141, 3088, 2983, 1601, 1496, 1388, 1246, 747, 697, 625 cm⁻¹
SI, p. S55
1-(2-phenylpropan-2-yl)-1H-indazole
Identifier 51
¹H NMR (500 MHz, CDCl₃) δ 7.94 (s, 1H), 7.76 (d, J = 9.0 Hz, 1H), 7.64 (d, J = 9.0 Hz, 1H), 7.32 – 7.23 (m, 4H), 7.10 – 7.04 (m, 3H), 2.13 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 148.2, 146.0, 128.5 (overlapped with 2C), 127.4, 125.7, 125.1, 121.5, 121.5, 120.2, 117.8, 65.3, 30.1
HRMS (ESI) m/z calcd for C₁₆H₁₇N₂ [M + H]⁺ 237.1386; found 237.1387
IR (ATR) νmax 3131, 3053, 2981, 1626, 1497, 1378, 1187, 760, 698 cm⁻¹
SI, p. S55
1-(2-phenylpropan-2-yl)-1H-1,2,3-triazole
Identifier 52
¹H NMR (500 MHz, CDCl₃) δ 7.72 (d, J = 1.0 Hz, 1H), 7.43 (d, J = 1.0 Hz, 1H), 7.33 (dd, J = 7.5, 7.5 Hz, 2H), 7.29 (t, J = 7.5 Hz, 1H), 7.11 (d, J = 7.5 Hz, 2H), 2.01 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 144.8, 133.7, 128.7, 127.8, 124.9, 122.3, 64.1, 29.8
HRMS (ESI) m/z calcd for C₁₁H₁₄N₃ [M + H]⁺ 188.1182; found 188.1181
IR (ATR) νmax 3150, 3061, 2939, 1601, 1497, 1371, 1206, 762, 698 cm⁻¹
SI, pp. S55–S56
methyl 2-(3-(1-amino-1-phenylethyl)phenyl)propanoate
Identifier 53
¹H NMR (500 MHz, CDCl₃) δ 7.36 (d, J = 8.0 Hz, 1H), 7.34 – 7.32 (m, 2H), 7.29 (dd, J = 8.0, 8.0 Hz, 2H), 7.25 – 7.19 (m, 3H), 7.16 (d, J = 6.5 Hz, 1H), 3.69 (q, J = 7.5 Hz, 1H), 3.63 (s, 3H), 1.85 (s, 3H), 1.78 (br s, 2H), 1.47 (d, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 175.0 (overlapped with 2C), 149.9, 149.4, 140.3 (overlapped with 2C), 128.3 (overlapped with 2C), 128.1(overlapped with 2C), 126.4 (overlapped with 2C), 126.1 (overlapped with 2C), 125.4 (overlapped with 2C), 125.4 (overlapped with 2C), 125.3 (overlapped with 2C), 125.2 (overlapped with 2C), 58.5 (overlapped with 2C), 51.9 (overlapped with 2C), 45.5 (overlapped with 2C), 31.7 (overlapped with 2C), 18.7, 18.6
HRMS (ESI) m/z calcd for C₁₈H₂₂NO₂ [M + H]⁺ 284.1645; found 284.1643
IR (ATR) νmax 3373, 3084, 2934, 1731, 1599, 1487, 1373, 1163, 767, 700 cm⁻¹
NMR reporting qualifier mixture of diastereoisomers
SI, p. S56
tert-butyl (2-(4-methoxyphenyl)propan-2-yl)glycinate
Identifier 54
¹H NMR (500 MHz, CDCl₃) δ 7.33 (d, J = 9.0 Hz, 2H), 6.86 (d, J = 9.0, 2H), 3.80 (s, 3H), 3.04 (s, 2H), 1.44 (s, 6H), 1.82 (br s, 1H), 1.42 (s, 9H)
¹³C NMR (125 MHz, CDCl₃) δ 172.1, 158.0, 139.0, 126.9, 113.5, 81.0, 55.2, 55.1, 46.1, 29.4, 28.0
HRMS (ESI) m/z calcd for C₁₅H₂₄NO₂ [M + H]⁺ 280.1907; found 280.1908
IR (ATR) νmax 3334, 3057, 2974, 1730, 1610, 1511, 1380, 1239, 1152, 736 cm⁻¹
SI, p. S57
methyl (2-([1,1'-biphenyl]-4-yl)propan-2-yl)-L-phenylalaninate
Identifier 55
¹H NMR (500 MHz, CDCl₃) δ 7.57 (d, J = 7.5 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 7.34 (t, J = 7.5 Hz, 1H), 7.28 (d, J = 8.5 Hz, 2H), 7.27 – 7.20 (m, 3H), 7.09 (dd, J = 7.5, 1.5 Hz, 2H), 3.51 (s, 3H), 3.25 (dd, J = 8.0, 6.0 Hz, 1H), 2.83 (dd, J = 13.0, 6.0 Hz, 1H), 2.76 (dd, J = 13.0, 8.0 Hz, 1H), 2.02 (br s, 1H), 1.40 (s, 3H), 1.35 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 176.9, 146.1, 140.9, 139.0, 137.4, 129.5, 128.7, 128.2, 127.1, 126.9, 126.6, 126.5, 126.5, 58.1, 56.1, 51.6, 41.5, 31.3, 27.7
HRMS (ESI) m/z calcd for C₂₅H₂₈NO₂ [M + H]⁺ 374.2115; found 374.2116
IR (ATR) νmax 3350, 3085, 2964, 1723, 1486, 1379, 1163, 763, 691 cm⁻¹
SI, p. S57
dimethyl (1,1-diphenylethyl)-L-aspartate
Identifier 56
¹H NMR (500 MHz, CDCl₃) δ 7.34 (d, J = 7.5 Hz, 2H), 7.31 (d, J = 7.5 Hz, 2H), 7.29 – 7.24 (m, 4H), 7.22 – 7.17 (m, 2H), 3.68 (s, 3H), 3.60 (dd, J = 6.5, 6.0 Hz, 1H), 3.46 (s, 3H), 2.76 (br s, 1H), 2.63 (dd, J = 15.0, 6.5 Hz, 1H), 2.54 (dd, J = 15.0, 6.0 Hz, 1H), 1.75 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 174.8, 171.2, 148.0, 147.1, 127.9, 127.9, 127.2, 127.2, 126.6, 126.5, 62.7, 52.9, 52.0, 51.7, 40.3, 27.9
HRMS (ESI) m/z calcd for C₂₀H₂₄NO₄ [M + H]⁺ 342.1700; found 342.1700
IR (ATR) νmax 3334, 3085, 2980, 1735, 1598, 1492, 1372, 1166, 761, 699 cm⁻¹
SI, p. S58
methyl (2-phenylpropan-2-yl)-L-valinate
Identifier 57
¹H NMR (500 MHz, CDCl₃) δ 7.46 (d, J = 7.5 Hz, 2H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 3.52 (s, 3H), 2.76 (d, J = 6.0 Hz, 1H), 1.74 – 1.67 (m, 1H), 1.42 (s, 3H), 1.41 (s, 3H), 0.88 (d, J = 7.0 Hz, 3H), 0.81 (d, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 177.3, 147.3, 127.8, 126.4, 126.4, 61.4, 55.7, 51.3, 32.9, 30.2, 28.4, 19.0, 18.8
HRMS (ESI) m/z calcd for C₁₅H₂₄NO₂ [M + H]⁺ 250.1802; found 250.1802
IR (ATR) νmax 3332, 3088, 2963, 1732, 1495, 1382, 1169, 764, 699 cm⁻¹
SI, p. S58
methyl (2-([1,1'-biphenyl]-4-yl)propan-2-yl)-L-methioninate
Identifier 58
¹H NMR (500 MHz, CDCl₃) δ 7.59 (d, J = 7.5 Hz, 2H), 7.54 (d, J = 9.0 Hz, 2H), 7.51 (d, J = 9.0 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.43 (t, J = 7.5, 1H), 3.56 (s, 3H), 3.18 (dd, J = 8.0, 5.5 Hz, 1H), 2.56 (ddd, J = 13.0, 8.5, 5.5 Hz, 1H), 2.49 (ddd, J = 13.0, 8.5, 5.5 Hz, 1H), 2.11 (br s, 1H), 2.03 (s, 3H), 1.80 – 1.67 (m, 2H), 1.46 (s, 3H), 1.45 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 177.2, 146.2, 140.8, 139.3, 128.7, 127.1, 127.0, 126.7, 126.6, 55.8, 54.9, 51.8, 34.7, 30.5, 30.3, 28.3, 15.2
HRMS (ESI) m/z calcd for C₂₁H₂₈NO₂S [M + H]⁺ 358.1835; found 358.1837
IR (ATR) νmax 3328, 3078, 2915, 1732, 1600, 1486, 1371, 1167, 766, 697 cm⁻¹
SI, p. S59
methyl (2-([1,1'-biphenyl]-4-yl)propan-2-yl)-L-serinate
Identifier 59
¹H NMR (500 MHz, CDCl₃) δ 7.58 (d, J = 7.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H), 7.50 (d, J = 8.5 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.34 (t, J = 7.5, 1H), 3.61 (s, 3H), 3.55 (dd, J = 10.0, 5.0 Hz, 1H), 3.47 (dd, J = 10.0, 6.0 Hz, 1H), 3.26 (dd, J = 6.0, 5.0 Hz, 1H), 2.83 (br s, 1H), 1.52 (br s, 1H), 1.51 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 174.8, 145.7, 140.6, 139.6, 128.7, 127.2, 127.0, 126.9, 126.5, 63.8, 57.4, 55.9, 52.2, 29.8, 29.2
HRMS (ESI) m/z calcd for C₁₉H₂₄NO₃ [M + H]⁺ 314.1751; found 314.1756
IR (ATR) νmax 3442, 3334, 3056, 2968, 1732, 1487, 1383, 1171, 766, 697 cm⁻¹
SI, pp. S59–S60
methyl (S)-3-((2-([1,1'-biphenyl]-4-yl)propan-2-yl)amino)-4-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoate
Identifier 60
¹H NMR (500 MHz, CDCl₃) δ 8.13 (d, J = 8.5 Hz, 1H), 7.57 (d, J = 8.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H), 7.46 – 7.40 (m, 4H), 7.36 – 7.29 (m, 3H), 7.26 (t, J = 7.0 Hz, 1H), 7.17 (d, J = 7.0 Hz, 2H), 4.85 (ddd, J = 8.5, 5.5, 5.5 Hz, 1H), 3.70 (s, 3H), 3.58 (s, 3H), 3.27 (dd, J = 6.0, 5.0 Hz, 1H), 3.15 (dd, J = 13.5, 5.5 Hz, 1H), 3.08 (dd, J = 13.5, 5.5 Hz, 1H), 2.65 (dd, J = 13.5, 6.0 Hz, 1H), 2.37 (dd, J = 13.5, 6.0 Hz, 1H), 2.29 (br s, 1H), 1.46 (s, 3H), 1.43 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 173.6, 171.9, 171.8, 145.9, 140.6, 139.6, 136.0, 129.4, 128.7, 128.5, 127.2, 127.1, 127.0, 126.9, 126.3, 56.0, 53.7, 52.6, 52.1, 51.7, 38.2, 37.6, 30.3, 27.5
HRMS (ESI) m/z calcd for C₃₀H₃₅N₂O₅ [M + H]⁺ 503.2541; found 503.2541
IR (ATR) νmax 3334, 3060, 2952, 1735, 1487, 1360, 1174, 767, 698 cm⁻¹
SI, p. S60
N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-phenylpropan-2-amine
Identifier 61
¹H NMR (500 MHz, CDCl₃) δ 7.32 – 7.26 (m, 4H), 7.22 – 7.18 (m, 1H), 6.71 (d, J = 7.5 Hz, 1H), 6.62 – 6.58 (m, 2H), 5.92 (s, 2H), 2.65 (t, J = 7.0 Hz, 2H), 2.64 (t, J = 7.0 Hz, 2H), 1.55 (br s, 1H), 1.43 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 147.5, 145.8, 133.8, 128.1, 126.1, 125.6 (overlapped with 2C), 121.6, 109.1, 108.1, 100.8, 55.7, 44.4, 36.6, 29.5
HRMS (ESI) m/z calcd for C₁₈H₂₂NO₂ [M + H]⁺ 284.1645; found 284.1644
IR (ATR) νmax 3327, 3084, 2967, 1602, 1487, 1379, 1243, 1184, 763, 699 cm⁻¹
SI, pp. S60–S61
N-(1-(4-methoxyphenyl)ethyl)-2-methyl-1-phenylpropan-2-amine
Identifier 62
¹H NMR (500 MHz, CDCl₃) δ 7.30 (d, J = 8.5 Hz, 2H), 7.26 (dd, J = 7.5, 7.5 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 7.15 (d, J = 7.5 Hz, 2H), 6.83 (d, J = 8.5 Hz, 2H), 4.01 (q, J = 6.5 Hz, 1H), 3.79 (s, 3H), 2.73 (d, J = 13.0 Hz, 1H), 2.60 (d, J = 13.0 Hz, 1H), 1.28 (d, J = 6.5 Hz, 3H), 0.94 (s, 3H), 0.90 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.0, 141.4, 138.7, 130.6, 127.8, 127.3, 126.0, 113.5, 55.2, 54.3, 51.5, 48.5, 28.0, 27.6, 27.5
HRMS (ESI) m/z calcd for C₁₉H₂₆NO [M + H]⁺ 284.2009; found 284.2008
IR (ATR) νmax 3340, 3083, 2961, 1610, 1509, 1364, 1239, 1169, 701 cm⁻¹
SI, p. S61
(1r,3R,5S,7r)-3,5-dimethyl-N-(2-phenylpropan-2-yl)adamantan-1-amine
Identifier 63
¹H NMR (500 MHz, CDCl₃) δ 7.50 (d, J = 7.5 Hz, 2H), 7.26 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 1.94 – 1.88 (m, 1H), 1.59 (br s, 1H), 1.52 (s, 6H), 1.27 (s, 2H), 1.21 (d, J = 12.0 Hz, 2H), 1.13 (s, 4H), 1.10 (d, J = 12.0 Hz, 2H), 0.99 (d, J = 12.0 Hz, 1H), 0.95 (d, J = 12.0 Hz, 1H), 0.70 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 151.3, 127.6, 125.8, 55.5, 54.3, 52.2, 50.6, 43.5, 42.7, 33.3, 32.4, 30.5, 30.4
HRMS (ESI) m/z calcd for C₂₁H₃₂N [M + H]⁺ 298.2530; found 298.2528
IR (ATR) νmax 3354, 3084, 2994, 1601, 1494, 1376, 1193, 763, 699 cm⁻¹
SI, pp. S61–S62
(N-(((2R,4aS,10aS)-7-isopropyl-2,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)methyl)-2-phenylpropan-2-amine
Identifier 64
¹H NMR (500 MHz, CDCl₃) δ 7.61 (d, J = 7.5 Hz, 2H), 7.55 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 8.0 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.33 (t, J = 7.5 Hz, 1H), 7.19 (d, J = 8.0 Hz, 1H), 6.99 (d, J = 8.0 Hz, 1H), 6.91 (s, 1H), 2.92 – 2.78 (m, 3H), 2.30 – 2.23 (m, 2H), 2.00 (d, J = 12.0 Hz, 1H), 1.81 – 1.69 (m, 2H), 1.67 – 1.48 (m, 5H), 1.44 (s, 6H), 1.42– 1.37 (m, 1H), 1.32– 1.27 (m, 1H), 1.24 (d, J = 7.0 Hz, 6H), 1.19 (s, 3H), 0.84 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 147.7, 147.6, 145.4, 141.0, 138.8, 134.9, 128.7, 127.0 (overlapped with 2C), 126.8, 126.6, 126.5, 124.3, 123.8, 55.1, 53.9, 44.4, 38.5, 37.4, 36.7, 36.0, 33.4, 30.3, 30.0, 29.5, 25.5, 24.0, 19.8, 18.9, 18.7
HRMS (ESI) m/z calcd for C₃₅H₄₆N [M + H]⁺ 480.3625; found 480.3625
IR (ATR) νmax 3342, 3054, 2958, 1601, 1496, 1380, 1178, 764, 696 cm⁻¹
SI, p. S62
ethyl 4-((2-phenylpropan-2-yl)amino)benzoate
Identifier 65
¹H NMR (500 MHz, CDCl₃) δ 7.65 (d, J = 8.0 Hz, 2H), 7.45 (dd, J = 8.0, 1.5 Hz, 2H), 7.32 (dd, J = 8.0, 8.0 Hz, 2H), 7.23 (t, J = 8.0 Hz, 1H), 6.29 (d, J = 9.0 Hz, 2H), 4.55 (br s, 1H), 4.26 (q, J = 7.0 Hz, 2H), 1.67 (s, 6H), 1.20 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 166.8, 149.9, 146.3, 130.8, 128.7, 126.6, 125.3, 118.4, 113.8, 60.0, 56.0, 30.6, 14.4
HRMS (ESI) m/z calcd for C₁₈H₂₂NO₂ [M + H]⁺ 284.1645; found 284.1644
IR (ATR) νmax 3370, 3085, 2983, 1683, 1603, 1366, 1267, 1171, 767, 699 cm⁻¹
SI, p. S63
methyl (2-phenylpropan-2-yl)-L-prolinate
Identifier 66
¹H NMR (500 MHz, CDCl₃) δ 7.52 (d, J = 7.5 Hz, 2H), 7.29 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 3.58 (dd, J = 8.5, 3.0 Hz, 1H), 3.56 (s, 3H), 2.94 (ddd, J = 8.5, 6.5, 3.0 Hz, 1H), 2.62 (ddd, J = 8.5, 8.5, 6.5 Hz, 1H), 1.99 – 1.87 (m, 2H), 1.87 – 1.78 (m, 1H), 1.74 – 1.65 (m, 1H), 1.43 (s, 3H), 1.37 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 177.5, 148.0, 127.8, 126.5, 126.3, 59.7, 58.8, 51.5, 48.1, 31.8, 25.7, 24.8, 23.8
HRMS (ESI) m/z calcd for C₁₅H₂₂NO₂ [M + H]⁺ 248.1645; found 248.1645
IR (ATR) νmax 3085, 2970, 1729, 1600, 1492, 1383, 1156, 765, 700 cm⁻¹
SI, p. S63
3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-(1-(4-methoxyphenyl)ethyl)-N-methylpropan-1-amine
Identifier 67
¹H NMR (500 MHz, CDCl₃) δ 7.13 – 7.08 (m, 4H), 7.07 – 7.02 (m, 4H), 6.89 (ddd, J = 7.5, 7.5, 1.0 Hz, 2H), 6.77 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 3.70 (t, J = 7.0 Hz, 2H), 3.43 (q, J = 7.0 Hz, 1H), 3.05 (s, 4H), 2.45 (ddd, J = 12.0, 7.5, 7.5 Hz, 1H), 2.23 (ddd, J = 12.0, 7.5, 7.5 Hz, 1H), 2.09 (s, 3H), 1.72 – 1.64 (m, 2H), 1.25 (d, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.3, 148.3, 136.1, 134.2, 129.7, 128.5, 126.2, 122.2, 119.9, 113.4, 62.7, 55.2, 51.9, 48.5, 38.4, 32.2, 25.6, 18.4
HRMS (ESI) m/z calcd for C₂₇H₃₃N₂O [M + H]⁺ 401.2588; found 401.2588
IR (ATR) νmax 3060, 2964, 1609, 1463, 1368, 1243, 1174, 832, 751 cm⁻¹
SI, p. S64
3-(9,10-ethanoanthracen-9(10H)-yl)-N-(1-(4-methoxyphenyl)ethyl)-N-methylpropan-1-amine
Identifier 68
¹H NMR (500 MHz, CDCl₃) δ 7.31 (d, J = 9.0 Hz, 2H), 7.25 (d, J = 7.5 Hz, 2H), 7.22 – 7.18 (m, 2H), 7.12 – 7.03 (m, 4H), 6.89 (d, J = 9.0 Hz, 2H), 4.26 (s, 1H), 3.82 (s, 3H), 3.65 (q, J = 7.0 Hz, 1H), 2.67 (ddd, J = 12.5, 7.5, 7.5 Hz, 1H), 2.54 (ddd, J = 12.5, 7.5, 7.5 Hz, 1H), 2.43 – 2.31 (m, 2H), 2.30 (s, 3H), 1.95 – 1.84 (m, 2H), 1.84 – 1.77 (m, 2H), 1.57 – 1.51 (m, 2H), 1.42 (d, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.4, 145.6, 145.0, 136.1, 128.8, 125.2, 125.1, 123.2, 121.4, 113.4, 62.7, 55.2, 55.2, 44.8, 44.5, 38.7, 29.6, 28.7, 27.7, 22.6, 18.6
HRMS (ESI) m/z calcd for C₂₉H₃₄NO [M + H]⁺ 412.2635; found 412.2635
IR (ATR) νmax 3066, 2974, 1609, 1509, 1463, 1369, 1238, 1176, 831, 756 cm⁻¹
SI, pp. S64–S65
(R)-N-methyl-3-phenyl-N-(2-phenylpropan-2-yl)-3-(o-tolyloxy)propan-1-amine
Identifier 69
¹H NMR (500 MHz, CDCl₃) δ 7.44 (d, J = 8.5 Hz, 2H), 7.29 – 7.24 (m, 4H), 7.22 – 7.18 (m, 1H), 7.16 (dd, J = 7.5, 7.5 Hz, 2H), 7.11 (t, J = 7.5 Hz, 1H), 7.05 (d, J = 7.5 Hz, 1H), 6.93 (t, J = 7.5 Hz, 1H), 6.73 (t, J = 7.5 Hz, 1H), 6.55 (d, J = 7.5 Hz, 1H), 5.18 (dd, J = 9.0, 3.5 Hz, 1H), 2.56 (ddd, J = 14.0, 8.0, 8.0 Hz, 1H), 2.43 (ddd, J = 12.5, 7.5, 4.0 Hz, 1H), 2.20 (s, 3H), 2.11 (s, 3H), 2.10 – 2.02 (m, 1H), 1.98 – 1.89 (m, 1H), 1.30 (s, 3H), 1.27 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 156.1, 149.7, 142.8, 130.4, 128.4, 127.8, 127.1, 127.0, 126.4, 126.0, 125.6, 119.8, 112.5, 77.1, 60.4, 47.6, 38.5, 35.0, 24.0, 23.9, 16.4
HRMS (ESI) m/z calcd for C₂₆H₃₂NO [M + H]⁺ 374.2479; found 374.2476
IR (ATR) νmax 3084, 2971, 1601, 1490, 1376, 1238, 1175, 764, 698 cm⁻¹
SI, p. S65
1-(2-((2,4-dimethylphenyl)thio)phenyl)-4-(2-phenylpropan-2-yl)piperazine
Identifier 70
¹H NMR (500 MHz, CDCl₃) δ 7.59 (d, J = 8.0 Hz, 2H), 7.36 (d, J = 7.5 Hz, 1H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 7.13 (s, 1H), 7.09 – 7.03 (m, 2H), 7.00 (d, J = 7.5 Hz, 1H), 6.85 – 6.80 (m, 1H), 6.49 (d, J = 8.0 Hz, 1H), 3.15 – 2.98 (m, 4H), 2.72 – 2.63 (m, 4H), 2.35 (s, 3H), 2.30 (s, 3H), 1.40 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.5, 149.3, 142.4, 139.1, 136.2, 134.4, 131.6, 128.1, 127.9, 127.7, 126.2, 126.1, 126.1, 125.4, 124.0, 119.7, 59.6, 52.5, 46.5, 24.2, 21.2, 20.6
HRMS (ESI) m/z calcd for C₂₇H₃₃N₂S [M + H]⁺ 417.2359; found 417.2360
IR (ATR) νmax 3081, 2974, 1601, 1469, 1373, 1240, 1187, 753, 701 cm⁻¹
SI, pp. S65–S66
(3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-(2-phenylpropan-2-yl)piperidine
Identifier 71
¹H NMR (500 MHz, CDCl₃) δ 7.57 (d, J = 7.5 Hz, 2H), 7.31 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 7.17 (dd, J = 8.5, 5.5 Hz, 2H), 6.96 (dd, J = 8.5, 8.5 Hz, 2H), 6.60 (d, J = 8.5 Hz, 1H), 6.27 (d, J = 2.5 Hz, 1H), 6.07 (dd, J = 8.5, 2.5 Hz, 1H), 5.87 (s, 2H), 3.53 (dd, J = 9.5, 2.5 Hz, 1H), 3.41 (dd, J = 9.5, 6.5 Hz, 1H), 3.24 – 3.18 (m, 1H), 2.92 – 2.86 (m, 1H), 2.46 – 2.37 (m, 1H), 2.23 – 2.08 (m, 3H), 1.79 – 1.72 (m, 2H), 1.393 (s, 3H), 1.386 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 161.4 (d, JC-F = 242.5 Hz), 154.4, 149.5, 148.0, 141.4, 140.2, 128.8 (d, JC-F = 7.5 Hz), 128.0, 126.1, 125.9, 115.2 (d, JC-F = 17.5 Hz), 107.8, 105.7, 101.0, 98.1, 69.9, 60.0, 50.5, 47.1, 44.7, 42.9, 35.3, 24.9, 23.7
¹⁹F NMR (376 MHz, CDCl₃) δ −116.93
HRMS (ESI) m/z calcd for C₂₈H₃₁NO₃F [M + H]⁺ 448.2281; found 448.2280
IR (ATR) νmax 3084, 2972, 1604, 1487, 1373, 1241, 1178, 766, 700 cm⁻¹
SI, p. S66
N-(2-(4-methoxyphenyl)propan-2-yl)butan-1-amine
Identifier 72
¹H NMR (500 MHz, CDCl₃) δ 7.33 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 2.30 (t, J = 7.5 Hz, 2H), 1.43 (s, 6H), 1.42 – 1.35 (m, 2H), 1.32 – 1.25 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 157.8, 140.1, 126.8, 113.3, 55.2, 55.2, 42.7, 33.1, 29.7, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₄H₂₄NO [M + H]⁺ 222.1853; found 222.1853
IR (ATR) νmax 3324, 3039, 2926, 1589, 1488, 1231, 1168, 752, 691 cm⁻¹
SI, p. S67
N-(2-(4-(methylthio)phenyl)propan-2-yl)butan-1-amine
Identifier 73
¹H NMR (500 MHz, CDCl₃) δ 7.35 (d, J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 2.48 (s, 3H), 2.30 (t, J = 7.0 Hz, 2H), 1.56 (br s, 1H), 1.44 (s, 6H), 1.42 – 1.35 (m, 2H), 1.32 – 1.24 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 145.0, 135.7, 126.5, 126.3, 55.5, 42.7, 33.0, 29.5, 20.5, 16.0, 14.0
HRMS (ESI) m/z calcd for C₁₄H₂₄NS [M + H]⁺ 238.1624; found 238.1622
IR (ATR) νmax 3316, 3076, 2957, 1596, 1491, 1378, 1182, 751, 698 cm⁻¹
SI, p. S67
N-(2-(4-(tert-butyl)phenyl)propan-2-yl)butan-1-amine
Identifier 74
¹H NMR (500 MHz, CDCl₃) δ 7.35 – 7.30 (m, 4H), 2.32 (t, J = 7.5 Hz, 2H), 1.45 (s, 6H), 1.44 – 1.37 (m, 2H), 1.32 (s, 9H), 1.31 – 1.25 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 148.7, 144.8, 125.3, 124.9, 55.4, 42.7, 34.3, 33.1, 31.4, 29.6, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₇H₃₀N [M + H]⁺ 248.2373; found 248.2372
IR (ATR) νmax 3315, 3088, 2956, 1510, 1464, 1182, 828, 696 cm⁻¹
SI, p. S68
N-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)butan-1-amine
Identifier 75
¹H NMR (500 MHz, CDCl₃) δ 7.60 (d J = 7.5 Hz, 2H), 7.56 (d, J = 8.0 Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H), 7.43 (dd, J = 7.5, 7.5 Hz, 2H), 7.33 (t, J = 7.5 Hz, 1H), 2.35 (t, J = 7.0 Hz, 2H), 1.49 (s, 6H), 1.46 – 1.39 (m, 2H), 1.35 – 1.27 (m, 2H), 0.87 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 147.2, 140.9, 138.8, 128.7, 127.0, 126.9, 126.8, 126.1, 55.5, 42.7, 33.1, 29.6, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₉H₂₆N [M + H]⁺ 268.2060; found 268.2063
IR (ATR) νmax 3327, 3078, 2957, 1601, 1486, 1378, 1181, 764, 733, 695 cm⁻¹
SI, p. S68
N-(2-(4-fluorophenyl)propan-2-yl)butan-1-amine
Identifier 76
¹H NMR (500 MHz, CDCl₃) δ 7.39 (dd, J = 8.5, 3.0 Hz, 2H), 6.99 (dd, J = 8.5, 8.5 Hz, 2H), 2.29 (t, J = 7.5 Hz, 2H), 1.43 (s, 6H), 1.42 – 1.36 (m, 2H), 1.32 – 1.25 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 160.3 (d, JC-F = 257.5 Hz), 143.8, 127.3 (d, JC-F = 7.5 Hz), 114.6 (d, JC-F = 21.3 Hz), 55.4, 42.6, 33.1, 29.8, 20.5, 14.0
¹⁹F NMR (125 MHz, CDCl₃) δ −117.73
HRMS (ESI) m/z calcd for C₁₃H₂₁NF [M + H]⁺ 210.1653; found 210.1653
IR (ATR) νmax 3333, 3058, 2959, 1601, 1507, 1379, 1222, 1182, 833, 697 cm⁻¹
SI, p. S69
N-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-yl)butan-1-amine
Identifier 77
¹H NMR (500 MHz, CDCl₃) δ 7.78 (d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 2.29 (t, J = 7.5 Hz, 2H), 1.47 (s, 6H), 1.44 – 1.38 (m, 2H), 1.34 (s, 12H), 1.30 – 1.26 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 134.7 (overlapped with 2C), 125.1, 83.7, 56.0, 42.8, 33.0, 29.5, 24.8, 20.5, 14.0
IR (ATR) νmax 3333, 3081, 2976, 1611, 1398, 1361, 1181, 1145, 660 cm⁻¹
HRMS (ESI) m/z calcd for C₁₉H₃₃BNO₂ [M + H]⁺ 318.2599; found 318.2599
¹³C NMR reporting qualifier The boron-bound carbon was not detected
SI, p. S69
4-(2-(butylamino)propan-2-yl)-N,N-dimethylaniline
Identifier 78
¹H NMR (500 MHz, CDCl₃) δ 7.28 (d, J = 9.0 Hz, 2H), 6.72 (d, J = 9.0 Hz, 2H), 2.93 (s, 6H), 2.31 (t, J = 7.5 Hz, 2H), 1.43 (s, 6H), 1.42 – 1.36 (m, 2H), 1.32 – 1.24 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 148.9, 135.6, 126.3, 112.3, 55.1, 42.7, 40.7, 33.0, 29.5, 20.6, 14.0
HRMS (ESI) m/z calcd for C₁₅H₂₇N₂ [M + H]⁺ 235.2169; found 235.2170
IR (ATR) νmax 3322, 3073, 2928, 1613, 1520, 1373, 1238, 1166, 818, 730 cm⁻¹
SI, p. S70
N-(1-(4-methoxyphenyl)ethyl)butan-1-amine
Identifier 79
¹H NMR (500 MHz, CDCl₃) δ 7.23 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H), 3.71 (q, J = 6.5 Hz, 1H), 2.48 (ddd, J = 14.0, 8.0, 5.0 Hz, 1H), 2.41 (ddd, J = 14.0, 8.0, 5.0 Hz, 1H), 1.49 – 1.38 (m, 2H), 1.33 (d, J = 6.5 Hz, 3H), 1.33 – 1.24 (m, 2H), 0.87 (t, J = 7.5, Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.4, 138.0, 127.5, 113.7, 57.7, 55.2, 47.5, 32.4, 24.3, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₃H₂₂NO [M + H]⁺ 208.1696; found 208.1695
IR (ATR) νmax 3328, 3062, 2928, 1611, 1510, 1463, 1368, 1242, 1178, 830, 752 cm⁻¹
SI, p. S70
N-(2-(benzo[d][1,3]dioxol-5-yl)propan-2-yl)butan-1-amine
Identifier 80
¹H NMR (500 MHz, CDCl₃) δ 6.97 (d, J = 1.5 Hz, 1H), 6.86 (dd, J = 8.0, 1.5 Hz, 1H), 6.75 (d, J = 8.0 Hz, 1H), 5.94 (s, 2H), 2.31 (t, J = 7.5 Hz, 2H), 1.54 (br s, 1H), 1.42 (s, 6H), 1.41 – 1.37 (m, 2H), 1.33 – 1.27 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 147.6, 145.6, 142.4, 118.6, 107.6, 106.6, 100.8, 55.6, 42.6, 33.1, 29.8, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₄H₂₂NO₂ [M + H]⁺ 236.1645; found 236.1645
IR (ATR) νmax 3326, 3073, 2958, 1610, 1487, 1374, 1236, 1181, 1039, 808 cm⁻¹
SI, p. S71
N-(2-(3,5-dimethoxyphenyl)propan-2-yl)butan-1-amine
Identifier 81
¹H NMR (500 MHz, CDCl₃) δ 6.59 (s, 2H), 6.33 (s, 1H), 3.80 (s, 6H), 2.32 (t, J = 7.0 Hz, 2H), 1.42 (s, 6H), 1.40 – 1.37 (m, 2H), 1.34 – 1.26 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 160.6, 150.9, 104.2, 97.5, 55.9, 55.2, 42.7, 33.1, 29.6, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₅H₂₆NO₂ [M + H]⁺ 252.1958; found 252.1959
IR (ATR) νmax 3326, 3088, 2956, 1593, 1454, 1378, 1202, 1150, 845 cm⁻¹
SI, p. S71
N-(1-mesitylethyl)butan-1-amine
Identifier 82
¹H NMR (500 MHz, CDCl₃) δ 6.80 (s, 2H), 4.29 (q, J = 7.0 Hz, 1H), 2.47 (ddd, J = 14.0, 8.0, 6.0 Hz, 1H), 2.45 – 2.33 (m, 1H), 2.40 (s, 6H), 2.24 (s, 3H), 1.48 – 1.41 (m, 2H), 1.38 (d, J = 7.0 Hz, 3H), 1.35 – 1.24 (m, 2H), 0.87 (t, J = 7.0, Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 137.5, 136.2, 135.5, 130.1, 54.0, 47.8, 32.7, 20.9, 20.7, 20.6, 20.4, 14.1
HRMS (ESI) m/z calcd for C₁₅H₂₆N [M + H]⁺ 220.2060; found 220.2059
IR (ATR) νmax 3301, 3005, 2957, 1611, 1464, 1376, 1142, 850, 732 cm⁻¹
SI, p. S72
N-(2-(naphthalen-2-yl)propan-2-yl)butan-1-amine
Identifier 83
¹H NMR (500 MHz, CDCl₃) δ 7.83 – 7.80 (m, 4H), 7.61 (dd, J = 8.5, 1.5 Hz, 1H), 7.45 (dd, J = 8.5, 8.5 Hz, 2H), 2.32 (t, J = 7.0 Hz, 2H), 1.55 (s, 6H), 1.44 – 1.38 (m, 2H), 1.31 – 1.24 (m, 2H), 0.84 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 145.5, 133.2, 132.1, 128.0, 127.8, 127.4, 125.8, 125.5, 124.5, 124.1, 55.8, 42.8, 33.1, 29.5, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₇H₂₄N [M + H]⁺ 242.1903; found 242.1901
IR (ATR) νmax 3329, 3050, 2957, 1599, 1462, 1377, 1239, 1180, 855, 745, 699 cm⁻¹
SI, p. S72
N-(2-(benzofuran-2-yl)propan-2-yl)butan-1-amine
Identifier 84
¹H NMR (500 MHz, CDCl₃) δ 7.50 (d, J = 8.5 Hz, 1H), 7.43 (d, J = 8.5 Hz, 1H), 7.23 (ddd, J = 7.5, 7.5, 1.5 Hz, 1H), 7.19 (ddd, J = 7.5, 7.5, 1.5 Hz, 1H), 6.47 (s, 1H), 2.34 (t, J = 7.5 Hz, 2H), 1.57 (br s, 1H), 1.51 (s, 6H), 1.43 – 1.37 (m, 2H), 1.30 – 1.23 (m, 2H), 0.83 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 163.5, 154.6, 128.5, 123.5, 122.4, 120.5, 111.0, 101.9, 53.5, 43.2, 32.7, 26.9, 20.4, 13.9
HRMS (ESI) m/z calcd for C₁₅H₂₂NO [M + H]⁺ 232.1697; found 232.1695
IR (ATR) νmax 3314, 3060, 2959, 1599, 1476, 1372, 1166, 1045, 751 cm⁻¹
SI, p. S73
N-(2-(thiophen-2-yl)propan-2-yl)butan-1-amine
Identifier 85
¹H NMR (500 MHz, CDCl₃) δ 7.17 (d, J = 4.5 Hz, 1H), 6.92 (dd, J = 4.5, 4.5 Hz, 1H), 6.88 – 6.84 (m, 1H), 2.43 (t, J = 7.0 Hz, 2H), 1.53 (s, 6H), 1.45 – 1.39 (m, 2H), 1.34 – 1.26 (m, 2H), 0.87 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 154.8, 126.3, 123.5, 122.8, 55.1, 42.8, 32.8, 30.3, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₁H₂₀NS [M + H]⁺ 198.1311; found 198.1310
IR (ATR) νmax 3313, 3103, 3070, 2958, 1462, 1378, 1240, 1182, 844, 691 cm⁻¹
SI, p. S73
N-(2-(6-methoxypyridin-3-yl)propan-2-yl)butan-1-amine
Identifier 86
¹H NMR (500 MHz, CDCl₃) δ 8.18 (d, J = 2.0 Hz, 1H), 7.68 (d, J = 8.5 Hz, 1H), 6.71 (d, J = 8.5 Hz, 1H), 3.93 (s, 3H), 3.60 (dd, J = 6.5, 6.0 Hz, 1H), 2.31 (t, J = 7.0 Hz, 2H), 1.44 (s, 6H), 1.42 – 1.34 (m, 2H), 1.33 – 1.24 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 162.7, 144.1, 136.9, 135.8, 110.2, 54.2, 53.3, 42.6, 33.0, 29.4, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₃H₂₃N₂O [M + H]⁺ 223.1805; found 223.1805
IR (ATR) νmax 3314, 3088, 2958, 1603, 1491, 1372, 1284, 1247, 1181, 830 cm⁻¹
SI, p. S74
N-(1,1-diphenylethyl)butan-1-amine
Identifier 87
¹H NMR (500 MHz, CDCl₃) δ 7.34 (d, J = 7.5 Hz, 4H), 7.28 (dd, J = 7.5, 7.5 Hz, 4H), 7.19 (t, J = 7.5, 7.5 Hz, 2H), 2.35 (t, J = 7.0 Hz, 2H), 1.79 (s, 3H), 1.50 (br s, 1H), 1.47 – 1.41 (m, 2H), 1.35 – 1.28 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 148.4, 127.9, 127.0, 126.2, 62.4, 42.7, 33.0, 27.6, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₈H₂₄N [M + H]⁺ 254.1903; found 254.1902
IR (ATR) νmax 3333, 3084, 2956, 1599, 1491, 1370, 1182, 759, 698 cm⁻¹
SI, p. S74
methyl 4-(1-(butylamino)-1-(4-methoxyphenyl)ethyl)benzoate
Identifier 88
¹H NMR (500 MHz, CDCl₃) δ 7.95 (d, J = 8.5 Hz, 2H), 7.44 (d, J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 6.82 (d, J = 8.5 Hz, 2H), 3.89 (s, 3H), 3.79 (s, 3H), 2.38 – 2.27 (m, 2H), 1.77 (s, 3H), 1.46 – 1.41 (m, 2H), 1.35 – 1.26 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 167.0, 158.0, 154.1, 139.7, 129.3, 128.0, 128.0, 127.0, 113.3, 62.1, 55.2, 52.0, 42.7, 33.0, 27.6, 20.5, 14.0
HRMS (ESI) m/z calcd for C₂₁H₂₈NO₂ [M + H]⁺ 342.2064; found 342.2063
IR (ATR) νmax 3332, 3092, 2954, 1721, 1608, 1509, 1276, 1247, 1179, 830 cm⁻¹
SI, p. S75
N-(1-phenyl-1-(thiophen-2-yl)ethyl)butan-1-amine
Identifier 89
¹H NMR (500 MHz, CDCl₃) δ 7.46 (d, J = 7.5, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.22 (t, J = 7.5, Hz, 1H), 7.19 (dd, J = 5.5, 1.0 Hz, 1H), 6.91 (dd, J = 5.5, 3.5 Hz, 1H), 6.80 – 6.76 (m, 1H), 2.45 (m, 2H), 1.86 (s, 3H), 1.57 (br s, 1H), 1.51 – 1.41 (m, 2H), 1.38 – 1.29 (m, 2H), 0.87 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 154.7, 147.6, 128.0, 126.7, 126.5, 126.2, 124.4, 124.0, 61.3, 42.9, 32.9, 29.0, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₆H₂₂NS [M + H]⁺ 260.1468; found 260.1467
IR (ATR) νmax 3329, 3084, 2926, 1600, 1464, 1236, 1180, 764, 696 cm⁻¹
SI, p. S75
N-butyl-5-methyl-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-amine
Identifier 90
¹H NMR (500 MHz, CDCl₃) δ 7.69 (d, J = 7.5 Hz, 2H), 7.19 (dd, J = 7.5, 7.5 Hz, 2H), 7.13 (dd, J = 7.5, 7.5 Hz, 2H), 7.08 (d, J = 7.5 Hz, 2H), 3.47 – 3.37 (m, 2H), 3.07 – 2.97 (m, 2H), 2.22 (t, J = 7.5 Hz, 2H), 1.82 (s, 3H), 1.56 (br s, 1H), 1.45 – 1.39 (m, 2H), 1.32 – 1.25 (m, 2H), 0.84 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 144.5, 141.8, 130.5, 127.7, 126.6, 126.0, 64.2, 43.0, 35.4, 32.9, 32.9, 20.5, 14.1
HRMS (ESI) m/z calcd for C₂₀H₂₆N [M + H]⁺ 280.2060; found 280.2057
IR (ATR) νmax 3323, 3056, 2953, 1601, 1482, 1448, 1375, 1204, 753 cm⁻¹
SI, p. S76
N-butyl-1-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
Identifier 91
¹H NMR (500 MHz, CDCl₃) δ 7.40 (d, J = 7.5 Hz, 1H), 7.17 (dd, J = 7.5, 7.5 Hz, 1H), 7.10 (dd, J = 7.5, 7.5 Hz, 1H), 7.05 (d, J = 7.5 Hz, 1H), 2.80 – 2.69 (m, 2H), 2.50 – 2.45 (m, 1H), 2.22 – 2.17 (m, 1H), 2.08 – 2.03 (m, 1H), 1.92 – 1.85 (m, 1H), 1.84 – 1.77 (m, 1H), 1.68 – 1.63 (m, 1H), 1.44 – 1.39 (m, 2H), 1.39 (br s, 1H), 1.38 (s, 3H), 1.34 – 1.28 (m, 2H), 0.86 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 142.9, 137.5, 128.9, 126.3, 126.0, 125.9, 55.1, 42.3, 34.8, 33.1, 31.5, 30.3, 20.6 (overlapped with 2C), 14.0
HRMS (ESI) m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1904
IR (ATR) νmax 3328, 3061, 2955, 1604, 1485, 1368, 1166, 759, 700 cm⁻¹
SI, pp. S76–S77
N-butyl-2-phenylhexan-2-amine
Identifier 92
¹H NMR (500 MHz, CDCl₃) δ 7.38 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 2.39 (ddd, J = 11.0, 7.0, 7.0 Hz, 1H), 2.19 (ddd, J = 11.0, 7.0, 7.0 Hz, 1H), 1.74 – 1.61 (m, 2H), 1.57 (br s, 1H), 1.44 (s, 3H), 1.42 – 1.36 (m, 2H), 1.33 – 1.26 (m, 2H), 1.26 – 1.19 (m, 2H), 1.17 – 1.09 (m, 1H), 1.07 – 0.97 (m, 1H), 0.86 (t, J = 7.0 Hz, 3H), 0.83 (t J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 147.1, 127.9, 126.2, 125.9, 58.3, 43.3, 42.2, 33.1, 26.1, 24.9, 23.2, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₆H₂₈N [M + H]⁺ 234.2216; found 234.2217
IR (ATR) νmax 3335, 3086, 2956, 1691, 1494, 1375, 1178, 763, 699 cm⁻¹
SI, p. S77
N-(1-cyclopropyl-1-phenylethyl)butan-1-amine
Identifier 93
¹H NMR (500 MHz, CDCl₃) δ 7.48 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 2.45 – 2.34 (m, 2H), 1.49 (br s, 1H), 1.47 – 1.40 (m, 2H), 1.36 – 1.28 (m, 2H), 1.24 (s, 3H), 1.19 (dddd, J = 8.5, 8.5, 5.5, 5.5 Hz, 1H), 0.87 (t, J = 7.5 Hz, 3H), 0.50 – 0.43 (m, 1H), 0.43 – 0.35 (m, 1H), 0.34 – 0.27 (m, 1H), 0.26 – 0.19 (m, 1H)
¹³C NMR (125 MHz, CDCl₃) δ 146.6, 127.8, 126.7, 126.1, 58.1, 42.3, 33.2, 23.9, 22.4, 20.6, 14.0, 2.2, 0.6
HRMS (ESI) m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1904
IR (ATR) νmax 3334, 3081, 2957, 1601, 1491, 1376, 1143, 762, 700 cm⁻¹
SI, pp. S77–S78
N-(1-cyclohexyl-1-phenylethyl)butan-1-amine
Identifier 94
¹H NMR (500 MHz, CDCl₃) δ 7.33 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 2.40 (ddd, J = 10.5, 7.0, 7.0 Hz, 1H), 2.10 (ddd, J = 10.5, 7.0, 7.0 Hz, 1H), 1.89 – 1.80 (m, 1H), 1.78 – 1.70 (m, 1H), 1.66 – 1.56 (m, 2H), 1.44 (dddd, J = 12.0, 12.0, 3.0, 3.0 Hz, 1H), 1.41 (s, 3H), 1.41 – 1.32 (m, 3H), 1.32 – 1.24 (m, 3H), 1.24 – 1.13 (m, 1H), 1.10 – 1.01 (m, 2H), 0.94 (dddd, J = 12.0, 12.0, 3.0, 3.0 Hz, 1H), 0.85 (t, J = 7.5 Hz, 3H), 0.88 – 0.79 (m, 1H)
¹³C NMR (125 MHz, CDCl₃) δ 146.5, 127.6, 127.0, 125.7, 61.1, 50.3, 42.2, 33.3, 27.9, 27.7, 27.0, 26.9, 26.7, 20.6, 20.4, 14.1
HRMS (ESI) m/z calcd for C₁₈H₃₀N [M + H]⁺ 260.2373; found 260.2375
IR (ATR) νmax 3344, 3085, 2952, 1600, 1492, 1374, 1180, 759, 700 cm⁻¹
SI, p. S78
methyl 3-(butylamino)-3-(4-methoxyphenyl)propanoate
Identifier 95
¹H NMR (500 MHz, CDCl₃) δ 7.24 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 4.02 (dd, J = 8.5, 5.5 Hz, 1H), 3.80 (s, 3H), 3.63 (s, 3H), 2.70 (dd, J = 15.5, 8.5 Hz, 1H), 2.59 (dd, J = 15.5, 5.5 Hz, 1H), 2.42 (ddd, J = 18.0, 11.5, 7.0 Hz, 1H), 2.41 (ddd, J = 18.0, 11.5, 7.0 Hz, 1H), 1.71 (br s, 1H), 1.46 – 1.37 (m, 2H), 1.35 – 1.23 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 172.4, 158.8, 134.9, 128.0, 113.8, 58.9, 55.2, 51.5, 47.1, 42.8, 32.2, 20.4, 13.9
HRMS (ESI) m/z calcd for C₁₅H₂₄NO₃ [M + H]⁺ 266.1751; found 266.1750
IR (ATR) νmax 3323, 3064, 2925, 1734, 1610, 1463, 1376, 1246, 1176, 831 cm⁻¹
SI, pp. S78–S79
methyl 3-(butylamino)-3-(4-methoxyphenyl)propanenitrile
Identifier 96
¹H NMR (500 MHz, CDCl₃) δ 7.32 (d, J = 8.5 Hz, 2H), 6.92 (d, J = 8.5 Hz, 2H), 3.99 (dd, J = 6.5, 6.5 Hz, 1H), 3.82 (s, 3H), 2.85 (dd, J = 17.0, 6.5 Hz, 1H), 2.79 (dd, J = 17.0, 6.5 Hz, 1H), 2.54 (ddd, J = 19.0, 6.5, 3.0 Hz, 1H), 2.52 (ddd, J = 19.0, 6.5, 3.0 Hz, 1H), 1.56 – 1.46 (m, 2H), 1.38 – 1.26 (m, 2H), 0.88 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 159.7, 131.3, 128.0, 117.5, 114.3, 58.7, 55.2, 47.0, 31.4, 26.2, 20.2, 13.8
HRMS (ESI) m/z calcd for C₁₄H₂₁N₂O [M + H]⁺ 233.1649; found 233.1649
IR (ATR) νmax 3323, 3064, 2927, 2248, 1611, 1512, 1463, 1375, 1246, 831 cm⁻¹
SI, p. S79
N-(1-(4-methoxyphenyl)propyl)butan-1-amine
Identifier 97
¹H NMR (500 MHz, CDCl₃) δ 7.19 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.81 (s, 3H), 3.42 (dd, J = 8.5, 6.0 Hz, 1H), 2.47 – 2.35 (m, 2H), 1.79 – 1.70 (m, 1H), 1.64 – 1.54 (m, 1H), 1.47 – 1.36 (m, 2H), 1.33 – 1.23 (m, 2H), 0.86 (t, J = 7.5 Hz, 3H), 0.78 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 158.4, 136.2, 128.2, 113.5, 64.6, 55.2, 47.4, 32.3, 30.9, 20.5, 14.0, 10.8
HRMS (ESI) m/z calcd for C₁₆H₂₄NO [M + H]⁺ 222.1853; found 222.1850
IR (ATR) νmax 3333, 3063, 2928, 1610, 1510, 1460, 1377, 1245, 1174, 828 cm⁻¹
SI, pp. S79–S80
N-butyl-1-phenylcyclopentan-1-amine
Identifier 98
¹H NMR (500 MHz, CDCl₃) δ 7.38 (d, J = 8.0 Hz, 2H), 6.84 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 2.21 (t, J = 7.0 Hz, 2H), 2.00 – 1.89 (m, 4H), 1.88 – 1.78 (m, 2H), 1.73 – 1.64 (m, 2H), 1.35 – 1.28 (m, 2H), 1.28 – 1.18 (m, 2H), 0.81 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 146.9, 127.9, 126.5, 126.0, 67.9, 43.1, 38.0, 33.0, 23.1, 20.5, 13.9
HRMS (ESI) m/z calcd for C₁₅H₂₄N [M + H]⁺ 218.1903; found 218.1901
IR (ATR) νmax 3083, 2955, 1600, 1493, 1377, 1176, 763, 698 cm⁻¹
SI, p. S80
N-butyl-1-phenylcyclohexan-1-amine
Identifier 99
¹H NMR (500 MHz, CDCl₃) δ 7.44 (d, J = 8.0 Hz, 2H), 7.32 (dd, J = 8.0, 8.0 Hz, 2H), 7.20 (t, J = 8.0 Hz, 1H), 2.16 (t, J = 7.0 Hz, 2H), 1.92 – 1.77 (m, 4H), 1.67 – 1.54 (m, 4H), 1.53 – 1.45 (m, 2H), 1.38 – 1.30 (m, 2H), 1.30 – 1.20 (m, 2H), 0.83 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 147.5, 128.0, 126.2, 125.9, 57.2, 41.3, 36.2, 33.1, 26.0, 22.2, 20.5, 14.0
HRMS (ESI) m/z calcd for C₁₆H₂₆N [M + H]⁺ 232.2060; found 232.2061
IR (ATR) νmax 3083, 2927, 1600, 1494, 1444, 1377, 1152, 758, 698 cm⁻¹
SI, p. S81
N-(1,1,2-triphenylethyl)butan-1-amine
Identifier 100
¹H NMR (500 MHz, CDCl₃) δ 7.28 – 7.21 (m, 8H), 7.17 (dd, J = 7.5, 7.5 Hz, 2H), 7.11 (t, J = 7.5 Hz, 1H), 7.06 (dd, J = 7.5, 7.5 Hz, 2H), 6.63 (d, J = 7.5 Hz, 2H), 3.57 (s, 2H), 2.37 (t, J = 7.5 Hz, 2H), 1.53 (br s, 1H), 1.43 – 1.37 (m, 2H), 1.34 – 1.27 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 146.9, 137.2, 130.5, 129.1, 128.3, 128.0, 127.6, 127.7, 127.5, 126.2, 126.6, 126.2, 65.5, 42.6, 42.3, 32.7, 20.5, 14.1
HRMS (ESI) m/z calcd for C₂₄H₂₈N [M + H]⁺ 330.2216; found 330.2219
IR (ATR) νmax 3327, 3086, 2953, 1601, 1495, 1236, 741, 695 cm⁻¹
SI, p. S81
N-butyl-4-(4-methoxyphenyl)-2-methylbut-3-yn-2-amine
Identifier 101
¹H NMR (500 MHz, CDCl₃) δ 7.33 (d, J = 9.0 Hz, 2H), 6.82 (d, J = 9.0 Hz, 2H), 3.81 (s, 3H), 2.77 (t, J = 7.5 Hz, 2H), 1.54 – 1.47 (m, 2H), 1.44 (s, 6H), 1.42 – 1.37 (m, 2H), 0.94 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 159.1, 132.9, 115.5, 113.8, 93.0, 81.7, 55.2, 50.3, 44.0, 32.6, 29.6, 20.6, 14.0
HRMS (ESI) m/z calcd for C₁₆H₂₄NO [M + H]⁺ 246.1853; found 246.1853
IR (ATR) νmax 3327, 3087, 2928, 1605, 1508, 1496, 1377, 1244, 830, 696 cm⁻¹
SI, p. S82
(8R,9S,13S,14S)-13-methyl-3-(2-morpholinopropan-2-yl)-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one
Identifier 102
¹H NMR (500 MHz, CDCl₃) δ 7.31 (d, J = 8.5 Hz, 1H), 7.24 – 7.19 (m, 2H), 3.67 (t, J = 4.0 Hz, 4H), 2.94 – 2.89 (m, 2H), 2.54 – 2.40 (m, 6H), 2.33 – 2.25 (m, 1H), 2.14 (ddd, J = 19.0, 9.0, 9.0 Hz, 1H), 2.10 – 2.00 (m, 2H), 1.98 – 1.94 (m, 1H), 1.67 – 1.57 (m, 2H), 1.57 – 1.40 (m, 4H), 1.33 (s, 6H), 0.91 (s, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 221.0, 145.9, 137.5, 135.8, 126.7, 124.9, 123.8, 67.8, 59.3, 50.5, 48.0, 46.6, 44.3, 38.2, 35.8, 31.6, 29.7, 26.7, 25.6, 23.9, 23.8, 21.6, 13.8
HRMS (ESI) m/z calcd for C₂₅H₃₆NO₂ [M + H]⁺ 382.2741; found 382.2740
IR (ATR) νmax 3085, 2952, 1738, 1603, 1496, 1375, 1244, 1176, 1114, 698 cm⁻¹
SI, pp. S82–S83
ethyl 3-(3,4-dimethoxyphenyl)-3-morpholinopropanoate
Identifier 103
¹H NMR (500 MHz, CDCl₃) δ 6.83 – 6.76 (m, 3H), 4.05 (q, J = 7.0 Hz, 2H), 3.88 (s, 3H), 3.87 (s, 3H), 3.72 (dd, J = 7.0, 7.0 Hz, 1H), 3.68 – 3.61 (m, 4H), 2.94 (dd, J = 14.5, 7.0 Hz, 1H), 2.61 (dd, J = 14.5, 7.0 Hz, 1H), 2.48 – 2.35 (m, 4H), 1.16 (t, J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 171.6, 148.7, 148.3, 131.5, 120.5, 111.3, 110.6, 67.1, 66.1, 60.3, 55.9, 55.8, 50.5, 38.5, 14.1
HRMS (ESI) m/z calcd for C₁₇H₂₆NO₅ [M + H]⁺ 324.1806; found 324.1804
IR (ATR) νmax 3053, 2955, 1732, 1605, 1513, 1463, 1255, 1114, 855 cm⁻¹
SI, p. S83
1'-methyl-10,11-dihydrospiro[dibenzo[a,d][7]annulene-5,2'-pyrrolidine]
Identifier 104
¹H NMR (500 MHz, CDCl₃) δ 7.34 (d, J = 8.0 Hz, 2H), 7.18 – 7.05 (m, 6H), 3.33 – 3.24 (m, 2H), 3.21 (t, J = 7.0 Hz, 2H), 3.15 – 3.07 (m, 2H), 2.45 (t, J = 7.0 Hz, 2H), 2.34 (s, 3H), 1.84 – 1.76 (m, 2H)
¹³C NMR (125 MHz, CDCl₃) δ 144.8, 140.8, 130.4, 128.3, 126.4, 125.7, 75.6, 54.0, 42.0, 36.9, 34.8, 22.4
HRMS (ESI) m/z calcd for C₁₉H₂₂N [M + H]⁺ 264.1747; found 264.1745
IR (ATR) νmax 3060, 2927, 1602, 1477, 1356, 1233, 1052, 752 cm⁻¹
SI, pp. S83–S84
N-(1-(4-(2-((2,2-diethoxyethyl)amino)propan-2-yl)-2,6-dimethylphenoxy)propan-2-yl)acetamide
Identifier 105
¹H NMR (500 MHz, CDCl₃) δ 7.04 (s, 2H), 5.95 (br s, 1H), 4.54 (dd, J = 5.5, 5.5 Hz, 1H), 4.38 – 4.29 (m, 1H), 3.79 (dd, J = 9.0, 3.5 Hz, 1H), 3.69 (dd, J = 9.0, 3.0 Hz, 1H), 3.65 – 3.58 (m, 2H), 3.52 – 3.44 (m, 2H), 2.46 (d, J = 5.5 Hz, 2H), 2.24 (s, 6H), 2.03 (s, 3H), 1.72 (br s, 1H), 1.42 (s, 6H), 1.40 (d, J = 7.0 Hz, 3H), 1.20 (t, J = 7.0 Hz, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 169.4, 153.0, 143.0, 129.9, 126.4, 102.7, 73.8, 62.0, 54.9, 45.5, 45.3, 29.5, 29.5, 23.4, 17.7, 16.4, 15.3
HRMS (ESI) m/z calcd for C₂₂H₃₉N₂O₄ [M + H]⁺ 395.2905; found 395.2903
IR (ATR) νmax 3463, 3288, 3076, 2973, 1648, 1548, 1486, 1372, 1192 cm⁻¹
SI, p. S84
methyl 2-(3-(1-((2-(tert-butoxy)-2-oxoethyl)amino)-1-phenylethyl)phenyl)propanoate
Identifier 106
¹H NMR (500 MHz, CDCl₃) δ 7.33 (d, J = 7.5 Hz, 2H), 7.31 – 7.26 (m, 3H), 7.24 – 7.18 (m, 3H), 7.18 – 7.14 (m, 1H), 3.69 (q, J = 7.0 Hz, 1H), 3.63 (s, 3H), 3.12 (s, 2H), 2.31 (br s, 1H), 1.77 (s, 3H), 1.46 (d, J = 7.0 Hz, 3H), 1.41 (s, 9H)
¹³C NMR (125 MHz, CDCl₃) δ 174.9 (overlapped with 2C), 171.8 (overlapped with 2C), 147.8, 147.7, 147.1, 147.1, 140.3, 140.3, 128.3, 128.3, 128.0 (overlapped with 2C), 127.1, 127.0, 126.5 (overlapped with 2C), 126.4, 126.4, 126.0, 126.0, 125.3 (overlapped with 2C), 81.1 (overlapped with 2C), 62.4 (overlapped with 2C), 51.9 (overlapped with 2C), 46.2 (overlapped with 2C), 45.5, 45.4, 28.0 (overlapped with 2C), 27.9, 27.8, 18.7, 18.5
HRMS (ESI) m/z calcd for C₂₄H₃₂NO₄ [M + H]⁺ 398.2336; found 398.2327
IR (ATR) νmax 3333, 3058, 2977, 1734, 1601, 1487, 1368, 1236, 1157, 703 cm⁻¹
NMR reporting qualifier mixture of diastereoisomers
SI, pp. S84–S85
methyl 5-(4-(1-((2-(benzo[d][1,3]dioxol-5-yl)ethyl)amino)ethyl)-2,5-dimethylphenoxy)-2,2-dimethylpentanoate
Identifier 107
¹H NMR (500 MHz, CDCl₃) δ 7.02 (s, 1H), 6.72 (d, J = 7.5 Hz, 1H), 6.65 (s, 1H), 6.62 (d, J = 7.5 Hz, 1H), 6.52 (s, 1H), 5.92 (s, 2H), 3.95 (q, J = 6.5 Hz, 1H), 3.91 – 3.86 (m, 2H), 3.66 (s, 3H), 2.75 – 2.61 (m, 4H), 2.25 (s, 3H), 2.16 (s, 3H), 1.74 – 1.67 (m, 4H), 1.55 (br s, 1H), 1.25 (d, J = 6.5 Hz, 3H), 1.21 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 178.3, 155.3, 147.6, 145.8, 134.6, 133.9, 133.2, 127.3, 124.4, 121.5, 112.8, 109.0, 108.1, 100.7, 67.9, 52.9, 51.7, 48.9, 42.1, 37.1, 36.1, 25.2, 25.1, 23.2, 19.0, 15.8
HRMS (ESI) m/z calcd for C₂₇H₃₈NO₅ [M + H]⁺ 456.2745; found 456.2747
IR (ATR) νmax 3322, 3061, 2950, 1728, 1613, 1488, 1389, 1249, 1194, 1139 cm⁻¹
SI, pp. S85–S86
N-benzyl-2-phenylpropan-2-amine hydrochloride
Identifier 108
¹H NMR (500 MHz, CDCl₃) δ 10.1 (br s, 2H), 7.79 (d, J = 7.5 Hz, 2H), 7.46 (d, J = 7.5 Hz, 2H), 7.40 – 7.34 (m, 3H), 7.23 (dd, J = 7.5, 7.5 Hz, 2H), 7.17 (t, J = 7.5 Hz, 1H), 3.60 – 3.54 (m, 2H), 1.73 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 139.3, 131.1, 130.5, 129.0, 128.8, 128.6, 128.4, 126.6, 62.6, 46.9, 26.1
HRMS (ESI) m/z calcd for C₁₆H₂₀N [M + H]⁺ 226.1590; found 226.1589
IR (ATR) νmax 3100 – 2400 (br), 3041, 2986, 1588, 1484, 1281, 756, 711 cm⁻¹
SI, p. S86
1-(2-phenylpropan-2-yl)piperidine
Identifier 109
¹H NMR (500 MHz, CDCl₃) δ 7.54 (d, J = 7.5 Hz, 2H), 7.30 (dd, J = 7.5, 7.5 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H), 2.50 – 2.30 (m, 4H), 1.56 – 1.47 (m, 4H), 1.45 – 1.37 (m, 2H), 1.33 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 150.0, 127.8, 126.0, 125.8, 59.9, 47.3, 27.0, 25.1, 24.2
HRMS (ESI) m/z calcd for C₁₄H₂₂N [M + H]⁺ 204.1747; found 204.1745
IR (ATR) νmax 3084, 2929, 1598, 1491, 1443, 1374, 1181, 760, 698 cm⁻¹
SI, pp. S86–S87
1-(hexan-2-yl)-4-methoxybenzene
Identifier 110
¹H NMR (500 MHz, CDCl₃) δ 7.10 (d, J = 8.5 Hz, 2H), 6.84 (dd, J = 8.5 Hz, 2H), 3.79 (s, 3H), 2.67 – 2.57 (m, 1H), 1.53 (dt, J = 7.5, 7.5 Hz, 2H), 1.31 – 1.22 (m, 2H), 1.20 (d, J = 7.0 Hz, 3H), 1.21 – 1.07 (m, 2H), 0.85 (t J = 7.0 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 157.5, 140.1, 127.8, 113.5, 55.2, 39.0, 38.3, 29.9, 22.8, 22.5, 14.1
SI, p. S87
4-(2-phenylpropan-2-yl)tetrahydro-2H-pyran
Identifier 111
¹H NMR (500 MHz, CDCl₃) δ 7.34 – 7.28 (m, 4H), 7.20 – 7.15 (m, 1H), 3.97 – 3.90 (m, 2H), 3.33 – 3.23 (m, 2H), 1.73 – 1.64 (m, 1H), 1.37 – 1.30 (m, 4H), 1.28 (s, 6H)
¹³C NMR (125 MHz, CDCl₃) δ 149.0, 127.9, 126.2, 125.5, 68.7, 46.7, 39.9, 28.0, 24.8
SI, p. S88
2-butyl-3-methyl-3-phenylisoindolin-1-one
Identifier 112
¹H NMR (500 MHz, CDCl₃) δ 7.81 (d, J = 7.5 Hz, 1H), 7.53 (dd, J = 7.5, 7.5 Hz, 1H), 7.43 (dd, J = 7.5, 7.5 Hz, 1H), 7.38 (d, J = 7.5 Hz, 1H), 3.45 – 3.40 (m, 2H), 1.75 – 1.67 (m, 2H), 1.49 (s, 6H), 1.46 – 1.38 (m, 2H), 0.97 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 167.5, 151.5, 131.4, 131.0, 127.9, 123.4, 120.5, 62.7, 39.4, 31.5, 26.0, 20.6, 13.9
HRMS (ESI) m/z calcd for C₁₄H₂₀NO [M + H]⁺ 218.1540; found 218.1540
IR (ATR) νmax 3056, 2957, 1683, 1613, 1495, 1467, 1388, 753, 695 cm⁻¹
SI, p. S88
1-butyl-4-methyl-4-phenylazetidin-2-one
Identifier 113
¹H NMR (500 MHz, CDCl₃) δ 7.41 – 7.36 (m, 4H), 7.34 – 7.29 (m, 1H), 3.26 (ddd, J = 20.5, 8.5, 6.5 Hz, 1H), 3.02 (d, J = 14.5 Hz, 1H), 2.99 (d, J = 14.5 Hz, 1H), 2.92 (ddd, J = 20.5, 8.5, 6.5 Hz, 1H), 1.85 (s, 3H), 1.57 – 1.45 (m, 2H), 1.34 – 1.26 (m, 2H), 0.87 (t, J = 7.5 Hz, 3H)
¹³C NMR (125 MHz, CDCl₃) δ 167.5, 142.0, 128.7, 127.6, 125.4, 58.8, 53.6, 40.5, 30.6, 23.2, 20.4, 13.6
HRMS (ESI) m/z calcd for C₁₄H₂₀NO [M + H]⁺ 218.1540; found 218.1539
IR (ATR) νmax 3060, 2957, 1740, 1602, 1497, 1447, 1378, 1244, 762, 699 cm⁻¹
SI, p. S89
Light on–off monitoring of product 3 from α-methylstyrene 1 and n-butylamine 2
¹H NMR monitoring, conditions PAZ (1.3 mg), 1 (47.4 mg, 0.401 mmol, 1 equiv), 2 (44.1 mg, 0.603 mmol, 1.5 equiv), and CH₃CN (1.0 mL) in a 10 mL Schlenk tube under N₂; 415 nm LEDs, <35 °C. At each indicated time point, a 50 μL aliquot was transferred to a J Young NMR tube, and the solvent was removed under vacuum, followed by 1,1,2,2-tetrachloroethane (50 μL of a 0.4 M solution in CDCl₃) as an internal standard and CDCl₃ (2.0 mL)
¹H NMR monitoring, light on–off sequence The product yield increased under irradiation, remained essentially unchanged in the dark, and increased again when irradiation was resumed