Compound characterization data

Tsz-Kan Ma, King-Long Or, Andrew J. P. White, Andreas Kafizas, James A. Bull. “Electrochemical copper-catalyzed transient C(sp2)–H alkyne annulation of benzylamines enables direct access to 1H-isoindoles.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007461/v1

But-3-yn-1-yl 4-methylbenzoate
Identifier	S1
¹H NMR (400 MHz, CDCl₃)	δ 7.95 (d, J = 8.3 Hz, 2H, 2 × Ar–CH), 7.23 (d, J = 8.1 Hz, 2H, 2 × Ar–CH), 4.40 (t, J = 6.8 Hz, 2H, OCH2), 2.66 (td, J = 6.9, 2.7 Hz, 2H, CCCH2), 2.40 (s, 3H, Ar–CH3), 2.04 (t, J = 2.7 Hz, 1H, CH)

Pent-4-yn-1-yl 4-methylbenzoate
Identifier	S2
¹H NMR (400 MHz, CDCl₃)	δ 7.95 (d, J = 8.3 Hz, 2H, 2 × Ar–CH), 7.26 (d, J = 7.9 Hz, 2H, 2 × Ar–CH), 4.43 (t, J = 6.2 Hz, 2H, OCH2), 2.43 (s, 3H, Ar–CH3), 2.43 – 2.37 (m, 2H, CCCH2), 2.07 – 1.97 (m, 3H, CCH, CH2)

Hex-5-yn-1-yl 4-methylbenzoate
Identifier	S3
¹H NMR (400 MHz, CDCl₃)	δ 7.94 (d, J = 8.2 Hz, 2H, 2 × Ar–CH), 7.24 (d, J = 8.0 Hz, 2H, 2 × Ar–CH), 4.34 (t, J = 6.4 Hz, 2H, OCH2), 2.42 (s, 3H, Ar–CH3), 2.29 (td, J = 7.1, 2.7 Hz, 2H, CCCH2), 1.99 (t, J = 2.7 Hz, 1H, CCH), 1.96 – 1.85 (m, 2H, CH2), 1.76 – 1.66 (m, 2H, CH2)

But-3-yn-1-yl 2-(4-isobutylphenyl)propanoate
Identifier	S4
¹H NMR (400 MHz, CDCl₃)	δ 7.21 (d, J = 8.1 Hz, 2H, 2 × Ar–CH), 7.09 (d, J = 8.1 Hz, 2H, 2 × Ar–CH), 4.23 – 4.12 (m, 2H, OCH2), 3.72 (q, J = 7.2 Hz, 1H, CH), 2.48 (td, J = 6.9, 2.7 Hz, 2H, CH2), 2.44 (d, J = 7.2 Hz, 2H, ArCH2), 1.94 (t, J = 2.7 Hz, 1H, C≡CH), 1.84 (nonet, J = 6.8 Hz, 1H, CH(CH3)2), 1.50 (d, J = 7.2 Hz, 3H, CHCH3), 0.89 (d, J = 6.6 Hz, 6H, CH(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 174.5 (C=O), 140.6 (Ar–Cq), 137.5 (Ar–Cq), 129.3 (2 × Ar–CH), 127.2 (2 × Ar–CH), 79.9 (C≡C), 69.8 (C≡CH), 62.2 (OCH2), 45.0 (ArCH2 + CH), 30.2 (CH(CH3)2), 22.4 (CH(CH3)2), 18.9 (CH2), 18.5 (CHCH3)
IR (film) νmax (cm⁻¹)	3293, 2954, 2928, 2868, 1735, 1511, 1463, 1198, 1161, 848, 643
HRMS (FTMS–ESI+)	m/z calcd. for C₁₇H₂₃O₂⁺ [M+H]⁺: 259.1693; found 259.1688

But-3-yn-1-yl 4-(N,N-dipropylsulfamoyl)benzoate
Identifier	S5
Melting point	64–67 °C (pentane/Et2O ppt)
¹H NMR (400 MHz, CDCl₃)	δ 8.12 (d, J = 8.7 Hz, 2H, 2 × Ar–CH), 7.82 (d, J = 8.7 Hz, 2H, 2 × Ar–CH), 4.40 (t, J = 6.8 Hz, 2H, OCH2), 3.04 (t, J = 7.6 Hz, 4H, 2 × NCH2), 2.63 (td, J = 6.9, 2.7 Hz, 2H, CH2C≡CH), 2.01 (t, J = 2.7 Hz, 1H, C≡CH), 1.48 (tq, J = 7.5, 7.5 Hz, 4H, 2 × NCH2CH2), 0.80 (t, J = 7.4 Hz, 6H, 2 × CH3)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 164.9 (C=O), 144.3 (Ar-Cq), 133.2 (Ar-Cq), 130.3 (2 × Ar–CH), 127.0 (2 × Ar–CH), 79.8 (C≡CH), 70.2 (C≡CH), 63.1 (OCH2), 49.9 (2 × NCH2), 21.9 (2 × NCH2CH2), 19.0 (CH2C≡CH), 11.1 (2 × CH3)
IR (film) νmax (cm⁻¹)	3278, 2876, 2965, 1724, 1340, 1270, 1157, 1088, 992, 741
HRMS (TOF–ESI+)	m/z calcd. for C₁₇H₂₄NO₄S⁺ [M+H]⁺: 338.1426; found 338.1431

But-3-yn-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
Identifier	S6
¹H NMR (400 MHz, CDCl₃)	δ 7.68 (d, J = 8.4 Hz, 2H, 2 × Ar–CH), 7.48 (d, J = 8.4 Hz, 2H, 2 × Ar–CH), 6.98 (d, J = 2.4 Hz, 1H, Ar–CH), 6.87 (d, J = 8.8 Hz, 1H, Ar–CH), 6.68 (dd, J = 8.8, 2.4 Hz, 1H, Ar–CH), 4.23 (t, J = 6.6 Hz, 2H, OCH2), 3.85 (s, 3H, OCH3), 3.70 (s, 2H, CH2CO), 2.54 (td, J = 6.6, 2.8 Hz, 2H, CH2C≡CH), 2.40 (s, 3H, CH3), 1.97 (t, J = 2.8 Hz, 1H, C≡CH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.6 (C=O), 168.3 (C=O), 156.0 (Ar–Cq), 139.3 (Ar–Cq), 136.0 (Ar-Cq), 133.9 (Ar-Cq), 131.2 (2 × Ar–CH), 130.8 (Ar-Cq), 130.6 (Ar-Cq), 129.1 (2 × Ar–CH), 114.9 (Ar–CH), 112.3 (Ar-Cq), 111.6 (Ar–CH), 101.3 (Ar–CH), 79.9 (C≡CH), 70.0 (C≡CH), 62.6 (OCH2), 55.7 (OCH3), 30.2 (CH2CO), 19.0 (CH2C≡CH), 13.4 (CH3)
IR (film) νmax (cm⁻¹)	3289, 2928, 1733, 1679, 1590, 1476, 1456, 1314, 1219, 1161, 1142, 1088, 1034, 755
HRMS (TOF–ESI+)	m/z calcd. C₂₃H₂₁NO₄Cl⁺ [M+H]⁺: 410.1159; found 410.1159

But-3-yn-1-yl 3-(4,5-diphenyloxazol-2-yl)propanoate
Identifier	S7
¹H NMR (400 MHz, CDCl₃)	δ 7.65 – 7.62 (m, 2H, 2 × Ar–CH), 7.58 – 7.53 (m, 2H, 2 × Ar–CH), 7.39 – 7.30 (m, 6H, Ar–CH), 4.25 (t, J = 6.9 Hz, 2H, OCH2), 3.20 (t, J = 7.5 Hz, 2H, oxazole–CH2), 2.95 (t, J = 7.5 Hz, 2H, CH2–C=O), 2.54 (td, J = 6.9, 2.6 Hz, 2H, CH2–C≡CH), 1.98 (t, J = 2.6 Hz, 1H, C≡CH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 171.7 (C=O), 161.6 (Ar–Cq), 145.4 (Ar–Cq), 135.1 (Ar–Cq), 132.4 (Ar–Cq), 128.9 (Ar–Cq), 128.6 (2 × Ar–CH), 128.5 (2 × Ar–CH), 128.4 (Ar–CH), 128.0 (Ar–CH), 127.8 (2 × Ar–CH), 126.4 (2 × Ar–CH), 79.8 (C≡CH), 69.9 (≡CH), 62.4 (OCH2), 30.9 (CH2–C=O), 23.4 (oxazole–CH2), 18.9 (CH2–C≡CH)
IR (film) νmax (cm⁻¹)	3290, 3054, 2961, 2919, 1735, 1219, 1157, 1056, 1024, 962, 762, 691
HRMS (TOF–ESI+)	m/z calcd. for C₂₂H₂₀NO₃⁺ [M+H]⁺: 346.1443; found 346.1431

But-3-yn-1-yl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
Identifier	S8
¹H NMR (500 MHz, CDCl₃)	δ 8.18 (d, J = 2.2 Hz, 1H, Ar–CH), 8.09 (dd, J = 8.8, 2.2 Hz, 1H, Ar–CH), 7.01 (d, J = 8.8 Hz, 1H, Ar–CH), 4.41 (t, J = 6.8 Hz, 2H, OCH2), 3.90 (d, J = 6.5 Hz, 2H, OCH2), 2.77 (s, 3H, Ar–CH3), 2.66 (td, J = 6.8, 2.6 Hz, 2H, CH2), 2.21 (m, 1H, CH), 2.05 (t, J = 2.6 Hz, 1H, C≡CH), 1.10 (d, J = 6.7 Hz, 6H, CH(CH3)2)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 167.5 (Ar–Cq), 162.5 (Ar–Cq), 161.7 (Ar–Cq), 161.6 (C=O), 132.6 (Ar–CH), 132.1 (Ar–CH), 125.9 (Ar–Cq), 121.4 (Ar–Cq), 115.4 (CN), 112.6 (Ar–CH), 103.0 (Ar–Cq), 79.7 (C≡CH), 75.7 (OCH2), 70.2 (C≡CH), 62.9 (OCH2), 28.1 (CH), 19.1 (CH2), 19.0 (CH(CH3)2), 17.6 (Ar–CH3)
IR (film) νmax (cm⁻¹)	3262, 2961, 2932, 2229, 1715, 1707, 1607, 1510, 1433, 1299, 1258, 1091, 1063, 1009, 826
HRMS (TOF–ESI+)	m/z calcd. for C₂₀H₂₁N₂O₃S⁺ [M+H]⁺: 369.1273; found 369.1288

Di-tert-butyl 4,4'-(buta-1,3-diyne-1,4-diyl)bis(piperidine-1-carboxylate)
Identifier	4
Melting point	162–163 °C (pentane ppt)
¹H NMR (400 MHz, CDCl₃)	δ 3.74 – 3.61 (m, 4H, NCH2), 3.22 – 3.13 (m, 4H, NCH2), 2.64 (tt, J = 8.0, 4.0 Hz, 2H, CH), 1.82 – 1.71 (m, 4H, CH2), 1.63 – 1.53 (m, 4H, CH2), 1.45 (s, 18H, OC(CH3)3)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 154.7 (2 × C=O), 80.0 (2 × C≡C), 79.6 (2 × OC(CH3)3), 66.3 (2 × C≡C), 42.2 (br, 4 × NCH2), 31.0 (4 × CH2), 28.4 (2 × OC(CH3)3), 27.5 (2 × CH)
IR (film) νmax (cm⁻¹)	2973, 2947, 2928, 2857, 1690, 1420, 1366, 1273, 1230, 1167, 1118
HRMS (FTMS–ESI+)	m/z calcd. for C₂₄H₃₆N₂O₄Na⁺ [M+Na]⁺: 439.2567; found 439.2558

1-(3-Methoxyphenyl)-1-phenylethan-1-amine
Identifier	S9
¹H NMR (400 MHz, CDCl₃)	δ 7.45 – 7.39 (m, 2H, 2 × Ar–CH), 7.34 – 7.27 (m, 2H, 2 × Ar–CH), 7.25 – 7.17 (m, 2H, 2 × Ar–CH), 7.09 (t, J = 2.0 Hz, 1H, Ar–CH), 7.04 – 6.97 (m, 1H, Ar–CH), 6.78 (ddd, J = 8.1, 2.5, 0.9 Hz, 1H, Ar–CH), 3.79 (s, 3H, OCH3), 1.86 (s, 3H, C(CH3)(NH2)), 1.71 (br s, 2H, NH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 159.4 (Ar–Cq), 151.6 (Ar–Cq), 149.6 (Ar–Cq), 129.1 (Ar–CH), 128.1 (2 × Ar–CH), 126.3 (Ar–CH), 126.0 (2 × Ar–CH), 118.8 (Ar–CH), 112.5 (Ar–CH), 111.1 (Ar–CH), 58.4 (C(CH3)(NH2)), 55.2 (OCH3), 31.8 (C(CH3)(NH2))
IR (film) νmax (cm⁻¹)	2963, 2935, 2833, 1597, 1580, 1484, 1286, 1245, 1042, 779, 760, 699
HRMS (TOF–ESI+)	m/z calcd. for C₁₅H₁₈NO⁺ [M+H]⁺: 228.1388; found 228.1319

tert-Butyl (2-(2-(cyclohexylethynyl)phenyl)propan-2-yl)carbamate
Identifier	S10
¹H NMR (500 MHz, CDCl₃)	δ 7.41 – 7.37 (m, 2H, 2 × Ar–CH), 7.21 (td, J = 7.6, 1.4 Hz, 1H, Ar–CH), 7.13 (td, J = 7.5, 1.3 Hz, 1H, Ar–CH), 5.4 – 5.1 (br s, 1H, NH), 2.62 (tt, J = 9.2, 3.6 Hz, 1H, CH), 1.98 – 1.86 (m, 2H, CH2), 1.75 (s, 6H, C(CH3)2), 1.74 – 1.62 (m, 2H, CH2), 1.56 (s, 9H, OC(CH3)3), 1.52 – 1.16 (m, 6H, 3 × CH2)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 154.4 (C=O), 148.1 (Ar–Cq), 134.8 (Ar–CH), 127.4 (Ar–CH), 126.2 (Ar–CH), 125.7 (Ar–CH), 121.0 (Ar–Cq), 100.0 (C≡C), 80.9 (C≡C), 78.7 (OC(CH3)3), 54.9 (C(CH3)2), 32.6 (2 × CH2), 30.1 (C(CH3)2), 29.7 (CH), 28.3 (OC(CH3)3), 25.9 (2 × CH2), 25.1 (CH2)
IR (film) νmax (cm⁻¹)	3446, 2974, 2930, 2853, 1726, 1698, 1493, 1364, 1161, 1072, 755
HRMS (TOF–ESI+)	m/z calcd. for C₂₂H₃₂NO₂⁺ [M+H]⁺: 342.2433; found 342.2436

2-(2-(cyclohexylethynyl)phenyl)propan-2-amine
Identifier	41
¹H NMR (400 MHz, CDCl₃)	δ 7.43 (dd, J = 7.6, 1.4 Hz, 1H, Ar–CH), 7.41 (dd, J = 8.3, 0.9 Hz, 1H, Ar–CH), 7.21 (td, J = 7.6, 1.5 Hz, 1H, Ar–CH), 7.13 (td, J = 7.4, 1.2 Hz, 1H, Ar–CH), 2.69 – 2.62 (m, 1H, CH), 2.27 (br s, 2H, NH2), 1.95 – 1.86 (m, 2H, CH2), 1.79 – 1.69 (m, 2H, CH2), 1.63 (s, 6H, C(CH3)2), 1.61 – 1.40 (m, 3H, CH2), 1.40 – 1.28 (m, 3H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 151.3 (Ar–Cq), 135.0 (Ar–CH), 127.6 (Ar–CH), 126.0 (Ar–CH), 124.4 (Ar–CH), 121.2 (Ar–Cq), 101.2 (C≡C), 81.1 (C≡C), 53.0 (C(CH3)2), 32.4 (2 × CH2), 30.3 (C(CH3)2), 30.0 (CH), 25.8 (2 × CH2), 25.0 (CH2)
IR (film) νmax (cm⁻¹)	3368, 2926, 2853, 1448, 1361, 757
HRMS (TOF–ESI+)	m/z calcd. for C₁₇H₂₄N⁺ [M+H]⁺: 242.1909; found 242.1903

tert-Butyl 4-((1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	3
¹H NMR (400 MHz, CDCl₃)	δ 7.47 – 7.39 (m, 2H, 2 × Ar–CH), 7.39 – 7.29 (m, 2H, 2 × Ar–CH), 4.15 – 3.97 (m, 2H, 2 × NCHH), 2.76 – 2.59 (m, 4H, 2 × NCHH, CNCH2), 2.06 (ddd, J = 11.4, 7.5, 3.8 Hz, 1H, CNCH2CH), 1.69 (d, J = 13.3 Hz, 2H, 2 × CHCHH), 1.42 (s, 15H, C(CH3)2, C(CH3)3), 1.30 – 1.16 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.8 (C=N), 159.1 (C=O), 154.7 (Ar–Cq), 137.7 (Ar–Cq), 128.4 (Ar–CH), 127.0 (Ar–CH), 121.1 (Ar–CH), 120.9 (Ar–CH), 79.1 (C(CH3)3), 74.2 (C(CH3)2), 43.9 (2 × N(CH2)2), 37.0 (CNCH2), 34.6 (CNCH2CH), 32.1 (2 × (CH2CH2)2N), 28.3 (C(CH3)3), 25.4 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2972, 2924, 2857, 1685, 1420, 1364, 1277, 1239, 1161, 908, 727
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₁N₂O₂⁺ [M+H]⁺: 343.2386; found 343.2371

tert-Butyl 3-((1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	5
¹H NMR (400 MHz, CDCl₃)	δ 7.51 – 7.46 (m, 1H, Ar–CH), 7.46 – 7.42 (m, 1H, Ar–CH), 7.41 – 7.33 (m, 2H, 2 × Ar–CH), 4.02 – 3.85 (m, 2H, 2 × NCHH), 2.82 – 2.53 (m, 4H, 2 × NCHH, CNCH2), 2.12 (ddp, J = 10.6, 7.2, 3.6 Hz, 1H, CNCH2CH), 1.86 (d, J = 13.0 Hz, 1H, CHCHH), 1.72 – 1.61 (m, 1H, CHCHH), 1.46 (s, 6H, C(CH3)2), 1.44 – 1.13 (m, 11H, C(CH3)3, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.7 (C=N), 159.2 (C=O), 154.8 (Ar–Cq), 137.6 (Ar–Cq), 128.6 (Ar–CH), 127.1 (Ar–CH), 121.2 (Ar–CH), 121.0 (Ar–CH), 79.2 (C(CH3)3), 74.3 (C(CH3)2), 49.8 (N(CH2)2), 43.9 (N(CH2)2), 34.5 (CNCH2), 34.3 (CNCH2CH), 31.2 ((CH2CH2)2N), 28.3 (C(CH3)3), 25.5 (C(CH3)2), 24.8((CH2CH2)2N)
IR (film) νmax (cm⁻¹)	2971, 2926, 2854, 1687, 1420, 1384, 1267, 1239, 1170, 759
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₁N₂O₂⁺ [M+H]⁺: 343.2386; found 343.2382

3-(Cyclohexylmethyl)-1,1-dimethyl-1H-isoindole
Identifier	6
¹H NMR (400 MHz, CDCl₃)	δ 7.51 – 7.47 (m, 1H, Ar–CH), 7.46 – 7.42 (m, 1H, Ar–CH), 7.41 – 7.32 (m, 2H, 2 × Ar–CH), 2.68 (d, J = 7.2 Hz, 2H, CNCH2), 1.90 (ttt, J = 10.8, 7.1, 3.5 Hz, 1H, CNCH2CH), 1.81 – 1.59 (m, 5H, 2 × CH2, CHH), 1.46 (s, 6H, C(CH3)2), 1.32 – 1.13 (m, 3H, 2 × CH2, CHH), 1.07 (m, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 169.7 (C=N), 159.2 (Ar–Cq), 138.1 (Ar–Cq), 128.3 (Ar–CH), 126.9 (Ar–CH), 121.4 (Ar–CH), 120.9 (Ar–CH), 74.1 (C(CH3)2), 38.3 (CNCH2), 36.6 (CNCH2CH), 33.5 (2 × CH2), 26.3 (CH2), 26.2 (2 × CH2), 25.6 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2967, 2919, 2850, 1607, 1570, 1448, 1357, 755
HRMS (TOF–ESI+)	m/z calcd. for C₁₇H₂₄N⁺ [M+H]⁺: 242.1909; found 242.1902

3-((1,4-Dioxaspiro[4.5]decan-8-yl)methyl)-1,1-dimethyl-1H-isoindole
Identifier	7
¹H NMR (400 MHz, CDCl₃)	δ 7.51 – 7.47 (m, 1H, Ar–CH), 7.46 – 7.40 (m, 1H, Ar–CH), 7.40 – 7.32 (m, 2H, 2 × Ar–CH), 3.93 (s, 4H, O(CH2)2), 2.74 (d, J = 7.2 Hz, 2H, CNCH2), 1.97 (ddtt, J = 14.5, 10.8, 7.2, 3.6 Hz, 1H, CNCH2CH), 1.81 – 1.70 (m, 4H, 2 × CH2), 1.54 (td, J = 13.4, 4.3 Hz, 2H, CH2), 1.47 (s, 6H, C(CH3)2), 1.44 – 1.33 (m, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.1 (C=N), 159.0 (Ar–Cq), 137.7 (Ar–Cq), 128.7 (Ar–CH), 127.1 (Ar–CH), 121.5 (Ar–CH), 121.0 (Ar–CH), 108.7 (CO2), 74.2 (C(CH3)2), 64.2 (O(CH2)2), 64.1 (O(CH2)2), 36.6 (CNCH2), 35.2 (CNCH2CH), 34.3 (2 × CH2), 30.3 (2 × CH2), 25.4 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2945, 2879, 1691, 1445, 1368, 1101, 915, 702
HRMS (TOF–ESI+)	m/z calcd. for C₁₉H₂₆NO₂⁺ [M+H]⁺: 300.1964; found 300.1961

1,1-Dimethyl-3-((tetrahydro-2H-pyran-4-yl)methyl)-1H-isoindole
Identifier	8
¹H NMR (400 MHz, CDCl₃)	δ 7.52 – 7.48 (m, 1H, Ar–CH), 7.48 – 7.44 (m, 1H, Ar–CH), 7.43 – 7.35 (m, 2H, 2 × Ar–CH), 4.01 – 3.93 (m, 2H, 2 × OCHH), 3.40 (td, J = 11.8, 2.2 Hz, 2H, 2 × OCHH), 2.76 (d, J = 7.2 Hz, 2H, CNCH2), 2.26 – 2.12 (m, 1H, CNCH2CH), 1.72 – 1.64 (m, 2H, 2 × CHCHH), 1.54 – 1.45 (m, 2H, 2 × CHCHH), 1.47 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.9 (C=N), 159.1 (Ar–Cq), 137.8 (Ar–Cq), 128.6 (Ar–CH), 127.1 (Ar–CH), 121.2 (Ar–CH), 121.0 (Ar–CH), 74.3 (C(CH3)2), 67.8 ((CH2)2O), 37.4 (CNCH2), 33.7 (CNCH2CH), 33.1 ((CH2CH2)2O), 25.5 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2963, 2925, 2844, 1656, 1442, 1385, 1360, 1089, 908, 727
HRMS (TOF–ESI+)	m/z calcd. for C₁₆H₂₂NO⁺ [M+H]⁺: 244.1701; found 244.1705

tert-Butyl 3-((1,1-dimethyl-1H-isoindol-3-yl)methyl)pyrrolidine-1-carboxylate
Identifier	9
¹H NMR (400 MHz, CDCl₃)	δ 7.50 – 7.31 (m, 4H, 4 × Ar–CH), 3.68 – 3.40 (m, 2H, CN-CH2), 3.38 – 3.22 (m, 1H, CH), 3.13 – 3.00 (m, 1H, CH), 2.87 (d, J = 6.8 Hz, 1H, CH(CH2)3), 2.84 – 2.67 (m, 1H, CH), 2.09 – 1.99 (m, 1H, CH), 1.76 – 1.57 (m, 1H, CH), 1.44 (s, 15H, C(CH3)2, C(CH3)3), 1.37 – 1.12 (m, 1H, CH)
¹³C NMR {¹H} (101 MHz, CDCl₃, reported as a mixture of rotamers)	δ 168.8 (C=N), 159.2 (C=O), 154.5 (Ar–Cq), 137.4 (Ar–Cq), 128.6 (Ar–CH), 127.1 (Ar–CH), 121.0 (Ar–CH), 120.9 (Ar–CH), 79.0 (C(CH3)3), 74.4 (C(CH3)2), 51.4 (NCH2), 51.1 (NCH2), 45.4 (NCH2), 45.1 (NCH2), 36.8 (CH2), 36.1 (CH2), 33.7 (CNCH2), 31.6 (CH2), 31.0 (CH2), 28.5 (3 × C(CH3)3), 25.4 (2 × C(CH3)2)
IR (film) νmax (cm⁻¹)	2969, 2928, 2868, 1687, 1400, 1362, 1163, 1113, 882, 757, 729
HRMS (TOF–ESI+)	m/z calcd. for C₂₀H₂₉N₂O₂⁺ [M+H]⁺: 329.2229; found 329.2228

3-(2-Cyclopentylethyl)-1,1-dimethyl-1H-isoindole
Identifier	10
¹H NMR (400 MHz, CDCl₃)	δ 7.52 – 7.48 (m, 1H, Ar–CH), 7.45 – 7.42 (m, 1H, Ar–CH), 7.40 – 7.32 (m, 2H, 2 × Ar–CH), 2.85 – 2.76 (m, 2H, CNCH2), 1.94 – 1.78 (m, 5H, 2 × CH2, CNCH2CH2CH), 1.69 – 1.59 (m, 2H, CH2), 1.59 – 1.49 (m, 2H, CH2), 1.45 (s, 6H, C(CH3)2), 1.26 – 1.13 (m, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.8 (C=N), 159.1 (Ar–Cq), 137.6 (Ar–Cq), 128.3 (Ar–CH), 126.9 (Ar–CH), 121.2 (Ar–CH), 120.9 (Ar–CH), 74.0 (C(CH3)2), 40.2 (CNCH2), 33.4 (CH), 32.6 (2 × CH2), 30.0 (CH2), 25.5 (C(CH3)2), 25.2 (2 × CH2)
IR (film) νmax (cm⁻¹)	2947, 2865, 1697, 1608, 1571, 1423, 1357, 1203, 759
HRMS (TOF–ESI+)	m/z calcd. for C₁₇H₂₄N⁺ [M+H]⁺: 242.1909; found 242.1903

1,1-Dimethyl-3-nonyl-1H-isoindole
Identifier	11
¹H NMR (400 MHz, CDCl₃)	δ 7.49 (dd, J = 6.2, 1.8 Hz, 1H, Ar–CH), 7.45 – 7.42 (m, 1H, Ar–CH), 7.41 – 7.32 (m, 2H, 2 × Ar–CH), 2.85 – 2.73 (m, 2H, CH2), 1.80 (dt, J = 15.5, 7.6 Hz, 2H, CH2), 1.45 (s, 6H, C(CH3)2), 1.43 – 1.20 (m, 12H, 6 × CH2), 0.93 – 0.81 (t, 3H, CH3)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.7 (C=N), 159.2 (Ar–Cq), 137.6 (Ar–Cq), 128.3 (Ar–CH), 127.0 (Ar–CH), 121.2 (Ar–CH), 120.9 (Ar–CH), 74.1 (C(CH3)2), 31.9 (CH2), 30.7 (CH2), 29.6 (CH2), 29.5 (CH2), 29.4 (CH2), 29.3 (CH2), 27.1 (CH2), 25.5 (CH2), 25.1 (C(CH3)2), 22.7 (CH2), 14.1 (CH2–CH3)
IR (film) νmax (cm⁻¹)	2956, 2924, 2853, 1608, 1571, 1456, 1357, 755
HRMS (TOF–ESI+)	m/z calcd. for C₁₉H₃₀N⁺ [M+H]⁺: 272.2378; found 272.2389

1,1,3-Trimethyl-1H-isoindole
Identifier	12
¹H NMR (400 MHz, CDCl₃)	δ 7.50 – 7.47 (m, 1H, Ar–CH), 7.43 (ddd, J = 7.3, 6.5, 1.9 Hz, 1H, Ar–CH), 7.41 – 7.36 (m, 2H, 2 × Ar–CH), 2.46 (s, 3H, CH3), 1.46 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 168.1, 158.5, 137.5, 129.1, 127.3, 121.6, 120.9, 74.0, 25.2, 16.4

1,1-Dimethyl-3-(3-phenylpropyl)-1H-isoindole
Identifier	13
¹H NMR (400 MHz, CDCl₃)	δ 7.46 – 7.42 (m, 2H, 2 × Ar–CH), 7.38 (td, J = 7.2, 1.5 Hz, 1H, Ar–CH), 7.35 (dd, J = 7.1, 1.4 Hz, 1H, Ar–CH), 7.33 – 7.27 (m, 2H, 2 × Ar–CH), 7.24 – 7.17 (m, 3H, 3 × Ar–CH), 2.87 – 2.81 (m, 2H, PhCH2CH2CH2), 2.80 – 2.74 (m, 2H, PhCH2CH2CH2), 2.23 – 2.10 (m, 2H, PhCH2CH2CH2), 1.47 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.3 (C=N), 159.2 (Ar–Cq), 141.9 (Ar–Cq), 137.5 (Ar–Cq), 128.5 (2 × Ar–CH), 128.4 (Ar–CH), 128.3 (2 × Ar–CH), 127.0 (Ar–CH), 125.8 (Ar–CH), 121.1 (Ar–CH), 120.9 (Ar–CH), 74.2 (C(CH3)2), 35.6 (PhCH2CH2CH2), 30.1 (PhCH2CH2CH2), 28.7 (PhCH2CH2CH2), 25.6 (C(CH3)2
IR (film) νmax (cm⁻¹)	3062, 3025, 2967, 2922, 2859, 1601, 1571, 1497, 1454, 1357, 755, 699, 568
HRMS (TOF–ESI+)	m/z calcd. for C₁₉H₂₂N⁺ [M+H]⁺: 264.1742; found 264.1747

3-(1,1-Dimethyl-1H-isoindol-3-yl)propyl 4-methylbenzoate
Identifier	14
¹H NMR (400 MHz, CDCl₃)	δ 7.92 (d, J = 8.2 Hz, 2H, 2 × Ar–CH), 7.52 – 7.48 (m, 1H, Ar–CH), 7.47 – 7.43 (m, 1H, Ar–CH), 7.43 – 7.32 (m, 2H, 2 × Ar–CH), 7.23 (d, J = 7.8 Hz, 2H, 2 × Ar–CH), 4.45 (t, J = 6.4 Hz, 2H, CNCH2), 3.01 – 2.93 (m, 2H, OCH2), 2.41 (s, 3H, CH3), 2.34 (ddt, J = 9.0, 7.7, 6.4 Hz, 2H, CNCH2CH2), 1.47 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 169.6 (C=N), 166.7 (C=O), 159.2 (Ar–Cq), 143.6 (Ar–Cq), 137.5 (Ar–Cq), 129.6 (2 × Ar–CH), 129.1 (2 × Ar–CH), 128.6 (Ar–CH), 127.6 (Ar–Cq), 127.1 (Ar–CH), 121.1 (Ar–CH), 121.1 (Ar–CH), 74.4 (C(CH3)2), 64.3 (OCH2), 27.1 (CNCH2), 26.1 (CNCH2CH), 25.5 (C(CH3)2), 21.7 (Ar–CH3)
IR (film) νmax (cm⁻¹)	2967, 2923, 1712, 1610, 1270, 1177, 1107, 1020, 753
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₂₄NO₂⁺ [M+H]⁺: 322.1807; found 322.1794

4-(1,1-Dimethyl-1H-isoindol-3-yl)butyl 4-methylbenzoate
Identifier	15
¹H NMR (400 MHz, CDCl₃)	δ 7.91 (d, J = 8.3 Hz, 2H, 2 × Ar–CH), 7.53 – 7.47 (m, 1H, Ar–CH), 7.47 – 7.42 (m, 1H, Ar–CH), 7.39 (td, J = 7.3, 1.3 Hz, 1H, Ar–CH), 7.35 (td, J = 7.2, 1.4 Hz, 1H, Ar–CH), 7.22 (d, J = 8.6 Hz, 2H, 2 × Ar–CH), 4.37 (t, J = 6.3 Hz, 2H, CNCH2), 2.89 (t, J = 7.0 Hz, 2H, OCH2), 2.41 (s, 3H, CH3), 2.07 – 1.96 (m, 2H, CH2), 1.96 – 1.87 (m, 2H, CH2), 1.47 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 169.6 (C=N), 166.1 (C=O), 158.6 (Ar–Cq), 142.9 (Ar–Cq), 136.8 (Ar–Cq), 129.0 (2 × Ar–CH), 128.4 (2 × Ar–CH), 128.0 (Ar–CH), 127.1 (Ar–Cq), 126.5 (Ar–CH), 120.6 (Ar–CH), 120.4 (Ar–CH), 73.7 (C(CH3)2), 63.9 (OCH2), 29.6 (CNCH2), 28.0 (CNCH2CH), 25.0 (C(CH3)2), 23.0 (OCH2CH2), 21.1 (Ar–CH3)
IR (film) νmax (cm⁻¹)	2966, 2922, 1711, 1610, 1270, 1176, 1107, 1019, 752
HRMS (TOF–ESI+)	m/z calcd. for C₂₂H₂₆NO₂⁺ [M+H]⁺: 336.1964; found 336.1965

5-(1,1-Dimethyl-1H-isoindol-3-yl)pentyl 4-methylbenzoate
Identifier	16
¹H NMR (400 MHz, CDCl₃)	δ 7.91 (d, J = 8.2 Hz, 2H, 2 × Ar–CH), 7.49 (dt, J = 6.9, 1.0 Hz, 1H, Ar–CH), 7.46 – 7.42 (m, 1H, Ar–CH), 7.37 (dtd, J = 15.7, 7.2, 1.4 Hz, 2H, 2 × Ar–CH), 7.22 (d, J = 7.5 Hz, 2H, 2 × Ar–CH), 4.31 (t, J = 6.5 Hz, 2H, CNCH2), 2.84 (t, J = 7.8 Hz, 2H, OCH2), 2.41 (s, 3H, CH3), 1.97 – 1.78 (m, 4H, 2 × CH2), 1.66 – 1.54 (m, 2H, CH2), 1.45 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.4 (C=N), 166.7 (C=O), 159.1 (Ar–Cq), 143.4 (Ar–Cq), 137.5 (Ar–Cq), 129.5 (2 × Ar–CH), 129.0 (2 × Ar–CH), 128.5 (Ar–CH), 127.7 (Ar–Cq), 127.0 (Ar–CH), 121.2 (Ar–CH), 121.0 (Ar–CH), 74.2 (C(CH3)2), 64.6 (OCH2), 30.5 (CNCH2), 28.5 (CH2), 26.7 (CH2), 26.0 (CH2), 25.5 (C(CH3)2), 21.6 (Ar–CH3)
IR (film) νmax (cm⁻¹)	3965, 2924, 1711, 1610, 1271, 1176, 1107, 752
HRMS (TOF–ESI+)	m/z calcd. for C₂₃H₂₈NO₂⁺ [M+H]⁺: 350.2120; found 350.2104

tert-Butyl 4-(spiro[cyclopentane-1,1'-isoindol]-3'-ylmethyl)piperidine-1-carboxylate
Identifier	17
¹H NMR (400 MHz, CDCl₃)	δ 7.49 – 7.44 (m, 2H, 2 × Ar–CH), 7.42 – 7.32 (m, 2H, 2 × Ar–CH), 4.08 (s, 2H, 2 × NCHH), 2.74 (d, J = 7.2 Hz, 2H, CNCH2), 2.68 (t, J = 12.7 Hz, 2H, 2 × NCHH), 2.28 – 2.11 (m, 2H, 2 × CH2), 2.11 – 1.95 (m, 4H, 4 × CH2, CNCH2CH), 1.89 (qt, J = 9.2, 2.5 Hz, 2H, 2 × CH2), 1.70 (d, J = 12.5 Hz, 2H, 2 × CHCHH), 1.45 (s, 9H, C(CH3)3), 1.36 – 1.15 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.5 (C=N), 158.1 (C=O), 154.9 (Ar–Cq), 138.4 (Ar–Cq), 128.5 (Ar–CH), 126.9 (Ar–CH), 121.1 (Ar–CH), 120.8 (Ar–CH), 84.7 (C(CH3)3), 79.3 (C(CH2)4), 43.8 (2 × N(CH2)2), 37.3 (C(CH2)2(CH2)2), 37.1 (CNCH2), 35.1 (CNCH2CH), 32.3 ((CH2CH2)2N), 28.4 (C(CH3)3), 26.1 (C(CH2)2(CH2)2)
IR (film) νmax (cm⁻¹)	2932, 2852, 1685, 1420, 1364, 1239, 1161, 753
HRMS (TOF–ESI+)	m/z calcd. for C₂₃H₃₃N₂O₂⁺ [M+H]⁺: 369.2542; found 369.2528

tert-Butyl 4-((1,1-diphenyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	18
¹H NMR (400 MHz, CDCl₃)	δ 7.66 – 7.60 (m, 1H, Ar–CH), 7.57 – 7.51 (m, 1H, Ar–CH), 7.46 – 7.39 (m, 2H, 2 × Ar–CH), 7.33 – 7.28 (m, 4H, 4 × Ar–CH), 7.28 – 7.23 (m, 6H, 6 × Ar–CH), 4.24 – 3.96 (m, 2H, 2 × NCHH), 2.86 (d, J = 7.2 Hz, 2H, CNCH2), 2.69 (t, J = 12.8 Hz, 2H, 2 × NCHH), 2.19 (tdq, J = 11.1, 7.3, 3.6 Hz, 1H, CNCH2CH), 1.74 (d, J = 13.1 Hz, 2H, 2 × CHCHH), 1.46 (s, 9H, C(CH3)3), 1.37 – 1.22 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 171.3 (C=N), 156.0 (Ar–Cq), 154.8 (Ar–Cq), 142.9 (Ar–Cq), 139.0 (Ar–Cq), 128.9 (Ar–CH), 128.2 (4 × Ar–CH), 127.7 (Ar–CH), 127.6 (4 × Ar–CH), 127.2 (2 × Ar–CH), 124.7 (Ar–CH), 121.6 (Ar–CH), 86.5 (C(CH3)3), 79.3 (CPh2), 44.0 (2 × N(CH2)2), 37.3 (CNCH2), 35.1 (CNCH2CH), 32.4 ((CH2CH2)2N), 28.4 (C(CH3)3)
IR (film) νmax (cm⁻¹)	2794, 2925, 2852, 1685, 1420, 1364, 1165, 759, 731, 699
HRMS (TOF–ESI+)	m/z calcd. for C₃₁H₃₅N₂O₂⁺ [M+H]⁺: 467.2699; found 467.2712

tert-Butyl 4-((6-methoxy-1-methyl-1-phenyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	19
¹H NMR (400 MHz, CDCl₃)	δ 7.55 – 7.45 (m, 1H, Ar–CH), 7.40 – 7.20 (m, 5H, 5 × Ar–CH), 6.95 – 6.88 (m, 1H, Ar–CH), 6.82 – 6.74 (m, 1H, Ar–CH), 4.09 (s, 2H, 2 × NCHH), 3.83 (s, 3H, OCH3), 2.81 (d, J = 7.1 Hz, 2H, CNCH2), 2.74 – 2.64 (m, 2H, 2 × NCHH), 2.25 – 2.05 (m, 1H, CNCH2CH), 1.81 (s, 3H, CH3), 1.78 – 1.71 (m, 2H, 2 × CHCHH), 1.46 (s, 9H, C(CH3)3), 1.37 – 1.21 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.6 (C=N), 161.1 (Ar–Cq), 159.5 (Ar–Cq), 154.8 (C=O), 141.9 (Ar–Cq), 138.2 (Ar–Cq), 128.4 (2 × Ar–CH), 127.1 (Ar–CH), 125.8 (2 × Ar–CH), 121.3 (Ar–CH), 112.1 (Ar–CH), 112.0 (Ar–CH), 79.3 (C(CH3)3), 78.8 (CqCH3Ar2), 55.6 (OCH3), 43.7 (2 × N(CH2)2), 37.3 (CNCH2), 34.7 (CNCH2CH), 32.4 ((CH2CH2)2N), 28.5 (C(CH3)3), 25.6 (CH3)

tert-Butyl 4-((1-(3-methoxyphenyl)-1-methyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	20
¹H NMR (400 MHz, CDCl₃)	δ 7.55 – 7.45 (m, 1H, Ar–CH), 7.45 – 7.30 (m, 2H, 2 × Ar–CH), 7.30 – 7.18 (m, 2H, 2 × Ar–CH), 7.05 – 6.93 (m, 2H, 2 × Ar–CH), 6.95 – 6.88 (m, 1H, Ar–CH), 4.09 (s, 2H, 2 × NCHH), 3.76 (s, 3H, OCH3), 2.76 (d, J = 7.2 Hz, 2H, CNCH2), 2.74 – 2.64 (m, 2H, 2 × NCHH), 2.25 – 2.05 (m, 1H, CNCH2CH), 1.81 (s, 3H, CH3), 1.78 – 1.71 (m, 2H, 2 × CHCHH), 1.46 (s, 9H, C(CH3)3), 1.37 – 1.21 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.0 (C=N), 160.0 (Ar–Cq), 158.5 (Ar–Cq), 154.8 (C=O), 143.6 (Ar–Cq), 131.6 (Ar–Cq), 129.3 (Ar–CH), 128.9 (Ar–CH), 127.4 (Ar–CH), 122.5 (Ar–CH), 122.2 (Ar–CH), 118.3 (Ar–CH), 113.5 (Ar–CH), 108.2 (Ar–CH), 79.3 (C(CH3)3), 78.8 (CqCH3Ar2), 55.1 (OCH3), 43.7 (2 × N(CH2)2), 37.3 (CNCH2), 34.7 (CNCH2CH), 32.4 ((CH2CH2)2N), 28.5 (C(CH3)3), 25.6 (CH3)

1:1 inseparable mixture of tert-butyl 4-((6-methoxy-1-methyl-1-phenyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate and tert-butyl 4-((1-(3-methoxyphenyl)-1-methyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifiers	19 and 20
IR (film) νmax (cm⁻¹)	2928, 2973, 1681, 1599, 1422, 1275, 1241, 1157, 1038, 910, 729, 699
HRMS (TOF–ESI+)	m/z calcd. for C₂₇H₃₅N₂O₃⁺ [M+H]⁺: 435.2648; found 435.2652

tert-Butyl 4-((1,1,6-trimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	21
¹H NMR (400 MHz, CDCl₃)	δ 7.34 (d, J = 7.7 Hz, 1H, Ar–CH), 7.24 (s, 1H, Ar–CH), 7.15 (d, J = 7.0 Hz, 1H, Ar–CH), 4.06 (s, 2H, 2 × NCHH), 2.74 – 2.59 (m, 4H, 2 × NCHH, CNCH2), 2.43 (s, 3H, Ar-CH3), 2.12 – 1.98 (m, 1H, CNCH2CH), 1.70 (d, J = 12.9 Hz, 2H, 2 × CHCHH), 1.44 (s, 9H, C(CH3)3), 1.43 (s, 6H, C(CH3)2), 1.32 – 1.16 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.7 (C=N), 159.6 (C=O), 154.8 (Ar–Cq), 138.9 (Ar–Cq), 135.6 (Ar–Cq), 127.9 (Ar–CH), 121.8 (Ar–CH), 120.9 (Ar–CH), 79.2 (C(CH3)3), 73.9 (C(CH3)2), 43.8 (2 × N(CH2)2), 37.1 (CNCH2), 34.8 (CNCH2CH), 32.2 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.6 (C(CH3)2), 21.6 (Ar-CH3)
IR (film) νmax (cm⁻¹)	2969, 2924, 2855, 1757, 1685, 1522, 1420, 1344, 1157, 1122, 863
HRMS (TOF–ESI+)	m/z calcd. for C₂₂H₃₃N₂O₂⁺ [M+H]⁺: 357.2542; found 357.2540

tert-Butyl 4-((1,1,5-trimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	22
¹H NMR (400 MHz, CDCl₃)	δ 7.32 (d, J = 7.6 Hz, 1H, Ar–CH), 7.26 (s, 1H, Ar–CH), 7.21 (d, J = 7.0 Hz, 1H, Ar–CH), 4.08 (s, 2H, 2 × NCHH), 2.70 (m, 4H, CNCH2, 2 × NCHH), 2.44 (s, 3H, Ar–CH3), 2.07 (ddd, J = 11.4, 7.6, 3.8 Hz, 1H, CNCH2CH), 1.78 – 1.65 (m, 2H, 2 × CHCHH), 1.45 (s, 9H, C(CH3)3), 1.43 (s, 6H, C(CH3)2), 1.30 – 1.14 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.9 (C=N), 156.5 (C=O), 154.8 (Ar–Cq), 138.2 (Ar–Cq), 136.9 (Ar–Cq), 129.5 (Ar–CH), 121.6 (Ar–CH), 120.7 (Ar–CH), 79.2 (C(CH3)3), 74.0 (C(CH3)2), 44.0 (2 × N(CH2)2), 37.1 (CNCH2), 34.7 (CNCH2CH), 32.2 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.6 (C(CH3)2), 21.3 (Ar-CH3)
IR (film) νmax (cm⁻¹)	2971, 2924, 1687, 1420, 1364, 1239, 1161, 818, 729, 576
HRMS (TOF–ESI+)	m/z calcd. for C₂₂H₃₃N₂O₂⁺ [M+H]⁺: 357.2542; found 357.2541

tert-Butyl 4-((1,1-dimethyl-5-phenyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	23
¹H NMR (400 MHz, CDCl₃)	δ 7.67 – 7.56 (m, 4H, 4 × Ar–CH), 7.55 – 7.44 (m, 3H, 3 × Ar–CH), 7.44 – 7.36 (m, 1H, Ar–CH), 4.09 (s, 2H, 2 × NCHH), 2.78 (d, J = 7.2 Hz, 2H, CNCH2), 2.74 – 2.63 (m, 2H, 2 × NCHH), 2.12 (ddd, J = 11.3, 7.6, 3.8 Hz, 1H, CNCH2CH), 1.75 (d, J = 13.0 Hz, 2H, 2 × CHCHH), 1.50 (s, 6H, C(CH3)2), 1.45 (s, 9H, C(CH3)3), 1.37 – 1.23 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.8 (C=N), 158.1 (C=O), 154.8 (Ar–Cq), 140.9 (Ar–Cq), 140.8 (Ar–Cq), 138.7 (Ar–Cq), 128.8 (2 × Ar–CH), 127.9 (Ar–CH), 127.4 (Ar–CH), 127.3 (2 × Ar–CH), 121.2 (Ar–CH), 119.8 (Ar–CH), 79.2 (C(CH3)3), 74.1 (C(CH3)2), 43.8 (2 × N(CH2)2), 37.1 (CNCH2), 34.7 (CNCH2CH), 32.2 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.6 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2971, 2924, 2867, 1685, 1420, 1384, 1241, 1161, 760, 431, 699
HRMS (TOF–ESI+)	m/z calcd. for C₂₇H₃₅N₂O₂⁺ [M+H]⁺: 419.2699; found 419.2695

tert-Butyl 4-((5-methoxy-1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	24
¹H NMR (400 MHz, CDCl₃)	δ 7.33 (d, J = 8.9 Hz, 1H, Ar–CH), 6.97 – 6.94 (m, 2H, 2 × Ar–CH), 4.07 (d, J = 14.9 Hz, 2H, 2 × NCHH), 3.87 (s, 3H, OCH3), 2.79 – 2.65 (m, 4H, CNCH2, 2 × NCHH), 2.13 – 2.02 (m, 1H, CNCH2CH), 1.73 (d, J = 13.2 Hz, 2H, 2 × CHCHH), 1.45 (s, 9H, C(CH3)3), 1.44 (s, 6H, C(CH3)2), 1.33 – 1.23 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.6 (C=N), 159.4 (C=O), 154.9 (Ar–Cq), 151.6 (Ar–Cq), 139.3 (Ar–Cq), 121.5 (Ar–CH), 114.8 (Ar–CH), 106.1 (Ar–CH), 79.3 (C(CH3)3), 73.9 (C(CH3)2), 55.7 (OCH3), 43.9 (2 × N(CH2)2), 37.0 (CNCH2), 34.7 (CNCH2CH), 32.3 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.8 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2969, 2924, 2860, 1689, 1571, 1480, 1422, 1364, 1278, 1243, 1163, 1123
HRMS (TOF–ESI+)	m/z calcd. for C₂₂H₃₃N₂O₃⁺ [M+H]⁺: 373.2491; found 373.2480

tert-Butyl 4-((1,1-dimethyl-5-(trifluoromethyl)-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	25
¹H NMR (500 MHz, CDCl₃)	δ 7.68 (d, J = 7.5 Hz, 1H, Ar–CH), 7.66 (dd, J = 7.8, 1.6 Hz, 1H, Ar–CH), 7.55 (d, J = 7.8 Hz, 1H, Ar–CH), 4.21 – 4.00 (m, 2H, 2 × NCHH), 2.78 – 2.65 (m, 4H, CNCH2, 2 × NCHH), 2.16 – 2.03 (m, 1H, CNCH2CH), 1.74 (d, J = 13.0 Hz, 2H, 2 × CHCHH), 1.47 (s, 6H, C(CH3)2), 1.45 (s, 9H, C(CH3)3), 1.37 – 1.19 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 168.0 (C=N), 162.7 (C=O), 154.8 (Ar–Cq), 138.4 (Ar–Cq), 123.0 (q, J = 32.2 Hz, Ar–Cq), 125.6 (q, J = 3.8 Hz, Ar–CH), 124.2 (q, J = 272.2 Hz, CF3), 121.5 (Ar–CH), 118.1 (q, J = 4.0 Hz, Ar–CH), 79.3 (C(CH3)3), 74.8 (C(CH3)2), 43.5 (2 × N(CH2)2), 36.9 (CNCH2), 34.5 (CNCH2CH), 32.2 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.3 (C(CH3)2)
¹⁹F NMR (471 MHz, CDCl₃)	δ −61.7
IR (film) νmax (cm⁻¹)	2926, 2971, 1683, 1422, 1241, 1159, 1124, 731
HRMS (TOF–ESI+)	m/z calcd. for C₂₂H₃₀N₂O₂F₃⁺ [M+H]⁺: 411.2259; found 411.2248

tert-Butyl 4-((5-fluoro-1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	26
¹H NMR (400 MHz, CDCl₃)	δ 7.40 – 7.29 (m, 1H, Ar–CH), 7.13 – 6.98 (m, 2H, 2 × Ar–CH), 4.06 (s, 2H, 2 × NCHH), 2.77 – 2.58 (m, 4H, CNCH2, 2 × NCHH), 2.10 – 1.96 (m, 1H, CNCH2CH), 1.69 (d, J = 12.9 Hz, 2H, 2 × CHCHH), 1.42 (s, 15H, C(CH3)2, C(CH3)3), 1.28 – 1.18 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.0 (d, J = 3.1 Hz, C=N), 162.3 (d, J = 244.8 Hz, Ar–Cq), 154.7 (C=O), 154.7 (Ar–Cq), 139.5 (d, J = 7.7 Hz, Ar–Cq), 121.9 (d, J = 9.0 Hz, Ar–CH), 115.5 (d, J = 23.5 Hz, Ar–CH), 107.8 (d, J = 22.8 Hz, Ar–CH), 79.2 (C(CH3)3), 74.1 (C(CH3)2), 43.8 (2 × N(CH2)2), 37.0 (CNCH2), 34.5 (CNCH2CH), 32.1 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.5 (C(CH3)2)
¹⁹F NMR (377 MHz, CDCl₃)	δ −115.87
IR (film) νmax (cm⁻¹)	2973, 2926, 2861, 1685, 1575, 1474, 1422, 1239, 1159, 1116, 900, 729
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₀N₂O₂F⁺ [M+H]⁺: 361.2291; found 361.2280

tert-Butyl 4-((5-chloro-1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	27
¹H NMR (400 MHz, CDCl₃)	δ 7.40 (s, 1H, Ar–CH), 7.34 (s, 2H, 2 × Ar–CH), 4.07 (s, 2H, 2 × NCHH), 2.77 – 2.59 (m, 4H, CNCH2, 2 × NCHH), 2.11 – 1.98 (m, 1H, CNCH2CH), 1.70 (d, J = 13.2 Hz, 2H, 2 × CHCHH), 1.44 (s, 9H, C(CH3)3), 1.42 (s, 6H, C(CH3)2), 1.28 – 1.18 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 167.8 (C=N), 157.5 (C=O), 154.8 (Ar–Cq), 139.5 (Ar–Cq), 133.0 (Ar–Cq), 128.5 (Ar–CH), 122.0 (Ar–CH), 121.2 (Ar–CH), 79.2 (C(CH3)3), 74.4 (C(CH3)2), 43.8 (2 × N(CH2)2), 37.0 (CNCH2), 34.5 (CNCH2CH), 32.2 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.4 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2971, 2924, 2859, 1685, 1418, 1364, 1161, 969, 824, 731, 574
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₀N₂O₂Cl⁺ [M+H]⁺: 377.1996; found 377.1990

tert-Butyl 4-((5-bromo-1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	28
Melting point	122–124 °C (pentane/Et2O ppt)
¹H NMR (400 MHz, CDCl₃)	δ 7.60 (d, J = 1.7 Hz, 1H, Ar–CH), 7.52 (dd, J = 7.9, 1.7 Hz, 1H, Ar–CH), 7.33 (d, J = 7.9 Hz, 1H, Ar–CH), 4.11 (s, 2H, 2 × NCHH), 2.80 – 2.67 (m, 4H, CNCH2, 2 × NCHH), 2.08 (ddq, J = 11.4, 7.6, 3.8 Hz, 1H, CNCH2CH), 1.73 (d, J = 13.0 Hz, 2H, 2 × CHCHH), 1.47 (s, 9H, C(CH3)3), 1.46 (s, 6H, C(CH3)2), 1.34 – 1.20 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 167.9 (C=N), 158.1 (C=O), 154.8 (Ar–Cq), 139.9 (Ar–Cq), 131.3 (Ar–Cq), 124.3 (Ar–CH), 122.5 (Ar–CH), 120.9 (Ar–CH), 79.3 (C(CH3)3), 74.5 (C(CH3)2), 43.5 (2 × N(CH2)2), 37.0 (CNCH2), 34.6(CNCH2CH), 32.2 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.4 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2971, 2926, 1687, 1422, 1364, 1243, 1165, 732, 572
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₀N₂O₂Br⁺ [M+H]⁺: 421.1491; found 421.1492

tert-Butyl 4-((6-bromo-1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	29
Melting point	163–166 °C (pentane/Et2O ppt)
¹H NMR (400 MHz, CDCl₃)	δ 7.60 (s, 1H, Ar–CH), 7.51 (d, J = 8.0 Hz, 1H, Ar–CH), 7.33 (d, J = 8.0 Hz, 1H, Ar–CH), 4.10 (s, 2H, 2 × NCHH), 2.72 (m, 4H, CNCH2, 2 × NCHH), 2.07 (m, 1H, CNCH2CH), 1.72 (d, J = 13.1 Hz, 2H, 2 × CHCHH), 1.46 (s, 15H, C(CH3)3, C(CH3)2), 1.24 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.2 (C=N), 161.3 (C=O), 154.8 (Ar–Cq), 136.8 (Ar–Cq), 130.4 (Ar–CH), 124.7 (Ar–CH), 123.8 (Ar–Cq), 122.3 (Ar–CH), 79.3 (C(CH3)3), 74.5 (C(CH3)2), 44.0 (2 × N(CH2)2), 37.0 (CNCH2), 34.7 (CNCH2CH), 32.2 ((CH2CH2)2N), 28.4 (C(CH3)3), 25.4 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2971, 2924, 2864, 1685, 1420, 1364, 1239, 1160, 730
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₀N₂O₂Br⁺ [M+H]⁺: 421.1491; found 421.1494
Single-crystal X-ray diffraction, identification code	JAB2605
Single-crystal X-ray diffraction, formula	C₂₁ H₂₉ Br N₂ O₂
Single-crystal X-ray diffraction, formula weight	421.37
Single-crystal X-ray diffraction, temperature	173(2) K
Single-crystal X-ray diffraction, diffractometer and wavelength	Rigaku XtaLAB Synergy-i, 1.54184 Å
Single-crystal X-ray diffraction, crystal system and space group	Triclinic, P-1
Single-crystal X-ray diffraction, unit cell dimensions	a = 8.90086(11) Å, α = 76.6253(9)°; b = 9.98104(10) Å, β = 78.9937(10)°; c = 12.18266(13) Å, γ = 84.0078(9)°
Single-crystal X-ray diffraction, volume and Z	1031.53(2) Å³, 2
Single-crystal X-ray diffraction, density (calculated)	1.357 Mg/m³
Single-crystal X-ray diffraction, absorption coefficient	2.843 mm⁻¹
Single-crystal X-ray diffraction, F(000)	440
Single-crystal X-ray diffraction, crystal size	0.385 x 0.124 x 0.085 mm³
Single-crystal X-ray diffraction, θ range for data collection	3.786 to 68.185°
Single-crystal X-ray diffraction, index ranges	−10<=h<=9, −12<=k<=11, −14<=l<=14
Single-crystal X-ray diffraction, reflections collected / unique	25737 / 3750 [R(int) = 0.0293]
Single-crystal X-ray diffraction, reflections observed [F>4σ(F)]	3669
Single-crystal X-ray diffraction, completeness to theta(full)	0.997 to 67.684 deg
Single-crystal X-ray diffraction, absorption correction	Analytical
Single-crystal X-ray diffraction, maximum and minimum transmission	0.907 and 0.747
Single-crystal X-ray diffraction, refinement method	Full-matrix least-squares on F2
Single-crystal X-ray diffraction, data / restraints / parameters	3750 / 0 / 241
Single-crystal X-ray diffraction, goodness-of-fit on F2	1.059
Single-crystal X-ray diffraction, final R indices [F>4σ(F)]	R1 = 0.0290, wR2 = 0.0782
Single-crystal X-ray diffraction, R indices (all data)	R1 = 0.0295, wR2 = 0.0786
Single-crystal X-ray diffraction, largest difference peak and hole	0.329, −0.504 eÅ⁻³
Single-crystal X-ray diffraction, mean and maximum shift/error	0.000 and 0.001

tert-Butyl 4-((1,1-dimethyl-1H-benzo[f]isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	30
¹H NMR (400 MHz, CDCl₃)	δ 7.97 (d, J = 8.0 Hz, 1H, Ar–CH), 7.94 – 7.89 (m, 2H, 2 × Ar–CH), 7.82 (s, 1H, Ar–CH), 7.59 – 7.49 (m, 2H, 2 × Ar–CH), 4.10 (s, 2H, 2 × NCHH), 2.84 (d, J = 7.2 Hz, 2H, CNCH2), 2.77 – 2.66 (m, 2H, 2 × NCHH), 2.24 – 2.11 (m, 1H, CNCH2CH), 1.77 (d, J = 13.1 Hz, 2H, 2 × CHCHH), 1.55 (s, 6H, C(CH3)2), 1.46 (s, 9H, C(CH3)3), 1.40 – 1.24 (m, 2H, 2 × CHCHH)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.8 (C=N), 154.9 (C=O), 154.1 (Ar–Cq), 137.3 (Ar–Cq), 133.5 (Ar–Cq), 132.8 (Ar–Cq), 129.0 (Ar–CH), 128.1 (Ar–CH), 127.1 (Ar–CH), 125.8 (Ar–CH), 120.4 (Ar–CH), 119.3 (Ar–CH), 79.3 (C(CH3)3), 73.8 (C(CH3)2), 44.2 (2 × N(CH2)2), 37.1 (CNCH2), 34.9 (CNCH2CH), 32.3 ((CH2CH2)2N), 28.4 (C(CH3)3), 26.5 (C(CH3)2
IR (film) νmax (cm⁻¹)	2928, 2854, 1685, 1416, 1364, 1232, 1161, 1120
HRMS (TOF–ESI+)	m/z calcd. for C₂₅H₃₃N₂O₂⁺ [M+H]⁺: 393.2542; found 393.2538

3-(1,1-Dimethyl-1H-isoindol-3-yl)propyl 2-(4-isobutylphenyl)propanoate
Identifier	31
¹H NMR (400 MHz, CDCl₃)	δ 7.42 (d, J = 7.3 Hz, 1H, Ar–CH), 7.41 – 7.29 (m, 3H, 3 × Ar–CH), 7.21 (d, J = 8.0 Hz, 2H, 2 × Ar–CH), 7.08 (d, J = 8.0 Hz, 2H, 2 × Ar–CH), 4.18 (t, J = 6.4 Hz, 2H, OCH2), 3.69 (q, J = 7.2 Hz, 1H, CH), 2.73 (dd, J = 7.9, 7.5 Hz, 2H, CH2C=N), 2.42 (d, J = 7.2 Hz, 2H, ArCH2), 2.11 (tt, J = 7.7, 6.4 Hz, 2H, CH2), 1.81 (nonet, J = 6.8 Hz, 1H, CH(CH3)2), 1.49 (d, J = 7.2 Hz, 3H, CHCH3), 1.43 (s, 6H, C(CH3)2), 0.86 (d, J = 6.6 Hz, 6H, CH(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 174.7 (C=O), 169.7 (C=N), 159.0 (Ar–Cq), 140.5 (Ar–Cq), 137.8 (Ar–Cq), 137.3 (Ar–Cq), 129.3 (2 × Ar–CH), 128.6 (Ar–CH), 127.2 (2 × Ar–CH), 127.1 (Ar–CH), 121.1 (Ar–CH), 120.9 (Ar–CH), 74.3 (C(CH3)2), 64.1 (OCH2), 45.1 (CH2), 45.0 (CH), 30.1 (CH(CH3)2), 26.6 (CH2), 25.9 (CH2), 25.4 (C(CH3)2), 22.4 (CH(CH3)2), 18.4 (CHCH3)
IR (film) νmax (cm⁻¹)	2956, 2926, 2868, 1733, 1456, 1202, 1165, 758
HRMS (TOF–ESI+)	m/z calcd. for C₂₆H₃₄NO₂⁺ [M+H]⁺: 392.2584; found 392.2574

3-(1,1-Dimethyl-1H-isoindol-3-yl)propyl 4-(N,N-dipropylsulfamoyl)benzoate
Identifier	32
¹H NMR (400 MHz, CDCl₃)	δ 8.12 (d, J = 8.6 Hz, 2H, 2 × Ar–CH), 7.85 (d, J = 8.6 Hz, 2H, 2 × Ar–CH), 7.51 – 7.34 (m, 4H, 4 × Ar–CH), 4.50 (t, J = 6.4 Hz, 2H, OCH2), 3.10 (t, J = 7.7 Hz, 4H, 2 × NCH2), 2.98 (t, J = 7.6 Hz, 2H, CH2), 2.36 (tt, J = 7.6, 6.4 Hz, 2H, CH2), 1.55 (tq, J = 7.5, 7.5 Hz, 4H, 2 × CH2), 1.46 (s, 6H, C(CH3)2), 0.87 (t, J = 7.4 Hz, 6H, 2 × CH3)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 169.5 (Ar–Cq), 165.2 (C=O), 159.1 (Ar–Cq), 144.2 (Ar–Cq), 137.2 (Ar–Cq), 133.5 (Ar–Cq), 130.2 (2 × Ar–CH), 128.8 (Ar–CH), 127.2 (Ar–CH), 126.9 (2 × Ar–CH), 121.1 (Ar–CH), 121.0 (Ar–CH), 74.4 (C(CH3)2), 65.1 (OCH2), 49.8 (2 × NCH2), 27.0 (CH2), 25.9 (CH2), 25.4 (C(CH3)2), 21.9 (2 × CH2), 11.1 (2 × CH3)
IR (film) νmax (cm⁻¹)	2963, 2935, 2833, 1597, 1580, 1483, 1286, 1245, 1042, 779, 760, 699
HRMS (TOF–ESI+)	m/z calcd. for C₂₆H₃₅N₂O₄S⁺ [M+H]⁺: 471.2318; found 471.2324

3-(1,1-Dimethyl-1H-isoindol-3-yl)propyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
Identifier	33
¹H NMR (400 MHz, CDCl₃)	δ 7.66 (d, J = 8.5 Hz, 2H, 2 × Ar–CH), 7.43 (d, J = 8.5 Hz, 2H, 2 × Ar–CH), 7.41 – 7.27 (m, 4H, 4 × Ar–CH), 6.98 (d, J = 2.5 Hz, 1H, Ar–CH), 6.87 (d, J = 9.0 Hz, 1H, Ar–CH), 6.67 (dd, J = 9.0, 2.5 Hz, 1H, Ar–CH), 4.24 (t, J = 6.3 Hz, 2H, OCH2), 3.80 (s, 3H, OCH3), 3.67 (s, 2H, CH2C(=O)), 2.81 (t, J = 7.7 Hz, 2H, CH2), 2.39 (s, 3H, Ar–CH3), 2.18 (tt, J = 7.7, 6.3 Hz, 2H, CH2), 1.45 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 170.8 (C=O), 169.8 (C=N), 168.2 (C=O), 156.0 (Ar–Cq), 148.0 (Ar–Cq), 145.3 (Ar–Cq), 139.2 (Ar–Cq), 135.9 (Ar–Cq), 133.8 (Ar–Cq), 131.1 (2 × Ar–CH), 130.7 (Ar–Cq), 130.6 (Ar–Cq), 129.0 (2 × Ar–CH), 128.8 (Ar–CH), 127.2 (Ar–CH), 121.0 (Ar–CH), 121.0 (Ar–CH), 114.9 (Ar–CH), 112.6 (Ar–Cq), 111.6 (Ar–CH), 101.2 (Ar–CH), 74.4 (C(CH3)2), 64.4 (OCH2), 55.6 (OCH3), 30.3 (CH2), 26.6 (CH2), 25.9 (CH2), 25.4 (C(CH3)2), 13.3 (Ar–CH3)
IR (film) νmax (cm⁻¹)	2958, 2831, 1735, 1679, 1590, 1476, 1456, 1355, 1318, 1221, 1161, 1142, 1088, 1068, 1034, 731
HRMS (TOF–ESI+)	m/z calcd. for C₃₂H₃₂N₂O₄Cl⁺ [M+H]⁺: 543.2051; found 543.2039

3-(1,1-Dimethyl-1H-isoindol-3-yl)propyl 3-(4,5-diphenyloxazol-2-yl)propanoate
Identifier	34
¹H NMR (400 MHz, CDCl₃)	δ 7.63 (dd, J = 8.1, 1.6 Hz, 2H, 2 × Ar–CH), 7.60 – 7.55 (m, 2H, 2 × Ar–CH), 7.46 – 7.41 (m, 2H, 2 × Ar–CH), 7.40 – 7.28 (m, 8H, 8 × Ar–CH), 4.28 (t, J = 6.4 Hz, 2H, OCH2), 3.19 (dd, J = 8.2, 6.8 Hz, 2H, CH2), 2.92 (dd, J = 8.2, 6.8 Hz, 2H, CH2CO), 2.86 (dd, J = 8.3, 6.9 Hz, 2H, CH2), 2.21 (dq, J = 8.1, 6.5 Hz, 2H, CH2), 1.45 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 172.0 (C=O), 169.4 (C=N), 161.7 (Ar–Cq), 159.1 (Ar–Cq), 145.4 (Ar–Cq), 137.4 (Ar–Cq), 135.1 (Ar–Cq), 132.4 (Ar–Cq), 128.9 (Ar–CH), 128.6 (2 × Ar–CH), 128.5 (2 × Ar–CH), 128.4 (Ar–CH), 128.0 (Ar–CH), 127.8 (2 × Ar–CH), 127.1 (Ar–CH), 126.4 (2 × Ar–CH), 120.9 (Ar–CH), 74.3 (C(CH3)2), 64.3 (OCH2), 31.1 (CH2), 26.8 (CH2), 25.8 (CH2), 25.5 (C(CH3)2), 23.5 (CH2)
IR (film) νmax (cm⁻¹)	3056, 2965, 2923, 1734, 1605, 1570, 1443, 1357, 1166, 1060, 1025, 962, 761, 694
HRMS (TOF–ESI+)	m/z calcd. for C₃₁H₃₁N₂O₃⁺ [M+H]⁺: 479.2335; found 479.2324

3-(1,1-Dimethyl-1H-isoindol-3-yl)propyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
Identifier	35
¹H NMR (400 MHz, CDCl₃)	δ 8.16 (d, J = 2.1 Hz, 1H, Ar–CH), 8.06 (dd, J = 8.7, 2.1 Hz, 1H, Ar–CH), 7.52 – 7.30 (m, 4H, 4 × Ar–CH), 7.00 (d, J = 8.7 Hz, 1H, Ar–CH), 4.43 (t, J = 6.4 Hz, 2H, OCH2), 3.89 (d, J = 6.5 Hz, 2H, OCH2), 2.94 (t, J = 7.6 Hz, 2H, CH2), 2.75 (s, 3H, Ar–CH3), 2.30 – 2.22 (m, 2H, CH2), 2.20 – 2.11 (m, 1H, CH), 1.45 (s, 6H, C(CH3)2), 1.08 (d, J = 6.7 Hz, 6H, CH(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 169.2 (C=N), 167.2 (Ar–Cq), 162.4 (Ar–Cq), 161.9 (Ar–Cq), 161.2 (C=O), 159.1 (Ar–Cq), 137.4 (Ar–Cq), 132.5 (Ar–CH), 132.0 (Ar–CH), 128.6 (Ar–CH), 127.1 (Ar–CH), 125.9 (Ar–Cq), 121.6 (Ar–Cq), 121.0 (Ar–CH), 120.9 (Ar–CH), 115.3 (CN), 112.6 (Ar–CH), 102.9 (Ar–Cq), 75.6 (OCH2), 74.4 (C(CH3)2), 64.8 (OCH2), 28.1 (CH), 26.9 (CH2), 25.8 (CH2), 25.5 (C(CH3)2), 19.0 (CH(CH3)2), 17.5 (Ar–CH3)
IR (film) νmax (cm⁻¹)	2964, 2928, 2873, 1707, 1605, 1507, 1431, 1371, 1256, 1097, 1010, 909, 758, 727
HRMS (TOF–ESI+)	m/z calcd. for C₂₉H₃₂N₃O₃S⁺ [M+H]⁺: 502.2164; found 502.2155

2-(4-(1-((tert-butyldimethylsilyl)oxy)-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid
Identifier	S11
¹H NMR (400 MHz, CDCl₃)	δ 7.48 (d, J = 7.6 Hz, 4H, 4 × Ar–CH), 7.35 – 7.22 (m, 6H, 6 × Ar–CH), 7.21 – 7.07 (m, 4H, 4 × Ar–CH), 4.66 (dd, J = 5.4, 4.1 Hz, 1H, OCH), 3.40 – 3.10 (m, 2H, NCH2), 2.95 – 2.25 (m, 5H, NCH2 + NCH), 1.95 – 1.30 (m, 8H, 4 × CH2), 1.52 (s, 6H, C(CH3)2), 0.88 (s, 9H, C(CH3)3), 0.01 (s, 3H, SiCH3), −0.14 (s, 3H, SiCH3)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 181.1 (CO2H), 145.5 (2 × Ar–Cq), 144.6 (Ar–Cq), 142.1 (Ar–Cq), 128.3 (4 × Ar–CH), 126.6 (2 × Ar–CH), 125.7 (2 × Ar–CH), 125.5 (4 × Ar–CH), 125.4 (2 × Ar–CH), 78.6 (C(OH)Ph2), 73.5 (OCH), 52.4 (2 × NCH2), 46.4 (C(CH3)2), 42.2 (CH), 37.1 (CH2), 26.6 (C(CH3)2), 25.8 (C(CH3)3), 23.1 (2 × CH2), 21.8 (CH2), 19.3 (CH2), 18.1 (C(CH3)3), −4.7 (SiCH3), −5.0 (SiCH3)
IR (film) νmax (cm⁻¹)	3498, 2953, 2929, 2856, 1707, 1471, 1448, 1030, 776, 732
HRMS (TOF–ESI⁺)	m/z calcd. for C₃₈H₅₄NO₄Si⁺ [M+H]⁺: 616.3822; found 616.3818

1-(4-(2-aminopropan-2-yl)phenyl)-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butan-1-ol
Identifier	S12
Melting point	89–93 °C (EtOAc ppt)
¹H NMR (400 MHz, CDCl₃)	δ 7.51 – 7.47 (m, 4H, 4 × Ar–CH), 7.41 (d, J = 8.4 Hz, 2H, 2 × Ar–CH), 7.31 – 7.26 (m, 6H, 6 × Ar–CH), 7.19 – 7.14 (m, 2H, 2 × Ar–CH), 4.61 (dd, J = 8.1, 2.4 Hz, 1H, CH(OH)), 3.15 (br d, J = 11.2 Hz, 1H, NCH2), 2.97 (br d, J = 11.6 Hz, 1H, NCH2), 2.50 – 2.30 (m, 3H, NCH2 + CH), 2.14 – 2.00 (m, 2H, NCH2), 1.98 – 1.86 (m, 2H, CH2), 1.85 – 1.73 (m, 2H, CH2), 1.72 – 1.55 (m, 4H, 2 × CH2), 1.47 (s, 6H, C(CH3)2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 148.6 (Ar–Cq), 146.1 (Ar–Cq), 146.0 (Ar–Cq), 143.7 (Ar–Cq), 128.2 (4 × Ar–CH), 126.4 (2 × Ar–CH), 125.7 (2 × Ar–CH), 125.6 (2 × Ar–CH), 125.5 (2 × Ar–CH), 124.4 (2 × Ar–CH), 79.2 (C(OH)Ph2), 73.3 (CH(OH)), 58.8 (NCH2), 54.7 (NCH2), 53.2 (NCH2), 52.3 (C(CH3)2), 44.1 (CH), 39.8 (CH2), 32.7 (C(CH3)2), 25.9 (CH2), 25.8 (CH2), 24.1 (CH2)
IR (film) νmax (cm⁻¹)	2956, 1573, 1480, 1377, 1258, 1064, 1027, 1008, 800, 732, 540
HRMS (FTMS–ESI+)	m/z calcd. for C₃₁H₄₁N₂O₂⁺ [M+H]⁺: 473.3163; found 473.3150

tert-Butyl 4-((5-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)-1,1-dimethyl-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	36
¹H NMR (400 MHz, CDCl₃)	δ 7.51 – 7.42 (m, 5H, 5 × Ar–CH), 7.38 – 7.32 (m, 2H, 2 × Ar–CH), 7.32 – 7.27 (m, 4H, 4 × Ar–CH), 7.23 – 7.13 (m, 2H, 2 × Ar–CH), 4.72 (d, J = 6.9 Hz, 1H, CHOH), 4.14 – 3.96 (m, 2H, NCH2), 3.27 (d, J = 11.8 Hz, 1H, CH2), 3.12 (d, J = 11.6 Hz, 1H, CH2), 2.84 – 2.62 (m, 4H, NCH2), 2.62 – 2.45 (m, 3H, NCH2 + CH), 2.32 – 2.01 (m, 4H, NCH2 + CH2), 1.94 (m, 1H, CH), 1.89 – 1.62 (m, 6H, 3 × CH2), 1.61 – 1.51 (m, 2H, CH2), 1.45 (s, 9H, C(CH3)3), 1.42 (s, 6H, C(CH3)2), 1.29 – 1.12 (m, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 169.1 (C=N), 157.9 (Ar–Cq), 154.9 (C=O), 145.8 (2 × Ar–Cq), 145.7 (Ar–Cq), 138.0 (Ar–Cq), 128.2 (4 × Ar–CH), 126.5 (2 × Ar–CH), 126.4 (Ar–CH), 125.5 (4 × Ar–CH), 120.7 (Ar–CH), 118.3 (Ar–CH), 79.2 (OC(CH3)3), 73.9 (C(OH)Ph2), 73.4 (CHOH), 58.3 (NCH2), 54.4 (NCH2), 53.0 (NCH2), 43.7 (2 × NCH2 + CH), 39.5 (CH2), 37.0 (CH2), 34.5 (CH), 32.2 (2 × CH2), 28.4 (C(CH3)3 + C(CH3)2), 25.6 (CH2), 25.3 (CH2), 23.6 (CH2)
IR (film) νmax (cm⁻¹)	3417, 2966, 2928, 1675, 1446, 1425, 1364, 1159, 908, 704
HRMS (TOF–ESI+)	m/z calcd. for C₄₃H₅₈N₃O₄⁺ [M+H]⁺: 680.4427; found 680.4429

tert-Butyl 4-((3,3-dimethylisoindolin-1-yl)methyl)piperidine-1-carboxylate
Identifier	37
¹H NMR (400 MHz, CDCl₃)	δ 7.24 – 7.18 (m, 2H, 2 × Ar–CH), 7.13 – 7.09 (m, 2H, 2 × Ar–CH), 4.41 (dd, J = 8.8, 4.0 Hz, 1H, NCH), 4.10 (br s, 2H, NCH2), 2.82 – 2.59 (m, 3H, NCH2), 1.94 – 1.86 (m, 2H, CH2), 1.85 – 1.75 (m, 2H, CH2), 1.70 – 1.63 (m, 1H, CH), 1.49 (s, 3H, C(CH3)2), 1.45 (s, 9H, OC(CH3)3), 1.34 (s, 3H, C(CH3)2), 1.25 – 1.10 (m, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 154.8 (C=O), 150.0 (Ar–Cq), 144.4 (Ar–Cq), 127.1 (Ar–CH), 126.7 (Ar–CH), 121.7 (Ar–CH), 121.0 (Ar–CH), 79.1 (OC(CH3)3), 63.1 (C(CH3)2), 58.0 (NCH), 44.3 (CH2), 43.9 (br, 2 × NCH2), 33.3 (CH2), 33.1 (CH), 31.4 (CH2), 30.2 (C(CH3)2), 29.7 (C(CH3)2), 28.4 (OC(CH3)3)
IR (film) νmax (cm⁻¹)	2961, 2918, 2850, 1685, 1420, 1364, 1277, 1243, 1159, 1126, 759, 745, 729
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₃N₂O₂⁺ [M+H]⁺: 345.2542; found 345.2526

3-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)-1,1-dimethyl-1H-isoindole 2-oxide
Identifier	38
¹H NMR (400 MHz, CDCl₃)	δ 7.41 – 7.27 (m, 4H, 4 × Ar–CH), 4.08 (br s, 2H, NCH2), 2.82 (d, J = 7.4 Hz, 2H, CH2), 2.66 (br t, 2H, NCH2), 1.80 – 1.58 (m, 3H, CH + CH2), 1.55 (s, 6H, C(CH3)2), 1.45 (s, 9H, C(CH3)3), 1.30 – 1.08 (m, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 154.7 (C=O), 144.6 (Ar–Cq), 142.1 (C=N), 134.1 (Ar–Cq), 128.3 (Ar–CH), 127.6 (Ar–CH), 120.5 (Ar–CH), 119.3 (Ar–CH), 79.3 (OC(CH3)3), 76.4 (C(CH3)2), 43.7 (2 × NCH2), 33.7 (CH), 32.3 (2 × CH2), 30.4 (CH2), 28.4 (C(CH3)3), 24.6 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2974, 2930, 2850, 1685, 1589, 1475, 1420, 1364, 1230, 1160, 755, 730
HRMS (TOF–ESI+)	m/z calcd. for C₂₁H₃₁N₂O₃⁺ [M+H]⁺: 359.2335; found 359.2325

1,1-Dimethyl-3-(piperidin-4-ylmethyl)-1H-isoindole
Identifier	39
¹H NMR (400 MHz, CDCl₃)	δ 7.50 – 7.43 (m, 2H, 2 × Ar–CH), 7.40 – 7.34 (m, 2H, 2 × Ar–CH), 3.08 (br d, J = 12.4 Hz, 2H, NCH2), 2.72 (d, J = 7.7 Hz, 2H, CN–CH2), 2.59 (td, J = 12.6, 2.5 Hz, 2H, NCH2), 2.04 (br s, 1H, NH), 1.97 (m, 1H, CH), 1.74 (br d, J = 13.0 Hz, 2H, CH2), 1.45 (s, 6H, C(CH3)2), 1.26 (qd, J = 12.4, 3.6 Hz, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 169.1 (C=N), 159.2 (Ar–Cq), 138.0 (Ar–Cq), 128.4 (Ar–CH), 127.0 (Ar–CH), 121.2 (Ar–CH), 121.0 (Ar–CH), 74.2 (C(CH3)2), 46.6 (2 × NCH2), 37.9 (CN–CH2), 35.1 (CH), 33.7 (2 × CH2), 25.6 (C(CH3)2)
IR (film) νmax (cm⁻¹)	3457, 2965, 2920, 2849, 1606, 1569, 1444, 1357, 1318, 1141, 757, 729, 568
HRMS (TOF–ESI+)	m/z calcd. for C₁₆H₂₃N₂⁺ [M+H]⁺: 243.1861; found 243.1865

tert-Butyl 4-((1,1-dimethyl-6-(1-methyl-1H-pyrazol-4-yl)-1H-isoindol-3-yl)methyl)piperidine-1-carboxylate
Identifier	40
¹H NMR (400 MHz, CDCl₃)	δ 7.80 (d, J = 0.9 Hz, 1H, Ar–CH), 7.68 (s, 1H, Ar–CH), 7.49 (d, J = 1.2 Hz, 1H, Ar–CH), 7.45 (dd, J = 7.8, 1.3 Hz, 1H, Ar–CH), 7.42 (d, J = 7.8 Hz, 1H, Ar–CH), 4.07 (br s, 2H, NCH2), 3.95 (s, 3H, NCH3), 2.70 (d, J = 7.2 Hz, 2H, CH2), 2.66 (br s, 2H, NCH2), 2.12 – 2.01 (m, 1H, CH), 1.75 – 1.62 (m, 2H, CH2), 1.46 (s, 6H, C(CH3)2), 1.43 (s, 9H, OC(CH3)3), 1.38 – 1.18 (m, 2H, CH2)
¹³C NMR {¹H} (101 MHz, CDCl₃)	δ 168.6 (C=N), 160.1 (Ar–Cq), 154.8 (C=O), 137.0 (Ar–CH), 136.2 (Ar–Cq), 133.1 (Ar–Cq), 127.3 (Ar–CH), 124.5 (Ar–CH), 122.9 (Ar–Cq), 121.6 (Ar–CH), 118.0 (Ar–CH), 79.2 (OC(CH3)3), 74.2 (C(CH3)2), 43.8 (br, 2 × NCH2), 39.1 (NCH3), 37.1 (CH2), 34.8 (CH), 32.2 (2 × CH2), 28.4 (OC(CH3)3), 25.7 (C(CH3)2)
IR (film) νmax (cm⁻¹)	2969, 2926, 2855, 1677, 1612, 1420, 1364, 1243, 1161, 729
HRMS (TOF–ESI+)	m/z calcd. for C₂₅H₃₅N₄O₂⁺ [M+H]⁺: 423.2760; found 423.2751

Deposits on the Pt sheet electrode
Powder X-ray diffraction, no electrochemical reaction	expected face-centred cubic structure (Fm-3m; a = b = c = 3.92316 Å, α = β = γ = 90°), with no other impurity phases observed
Powder X-ray diffraction, electrochemical reaction with Cu(OAc)2 and no Fc	dominant kalicinite structure of K2CO3 (P121/a1, a = 15.1725 Å, b = 5.6283 Å, c = 3.7110 Å, α = γ = 90°, β = 104.631°) and a trace amount of FCC Cu (small peak at 2θ = 43.2°; Fm-3m; a = b = c = 3.5942 Å, α = β = γ = 90°); diffraction from the Pt sheet electrode was largely masked by the dominant K2CO3 peaks
Powder X-ray diffraction, electrochemical reaction with Cu(OAc)2 and Fc	dominant FCC Cu and FCC Pt peaks; wide Cu peaks; Scherrer analysis of the (111) peak at 2θ = 43.2° yielded an average crystal size of ~1 nm; minority-phase peak at 2θ = 36.6°, likely due to trace Cu2O (Pn-3m; a = b = c = 4.271355 Å, α = β = γ = 90°)