Compound characterization data — Koutiva and Teskey, 2026

Maria Koutiva, Christopher J. Teskey. “Merging CO₂ reduction and carbonylation into a single catalytic platform.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007993/v1

The NMR spectrum images for compounds 1a–2aq in the SI, pp. S39–S155, were not transcribed. The sample identity for the labelling experiment in the SI, pp. S156–S157, is presented graphically; its associated NMR and HRMS data were not transcribed

2,4-difluorophenyl cyclohexanecarboxylate
Identifier	1a
¹H NMR (600 MHz, CDCl₃)	δ 7.06 (td, J = 8.8, 5.5 Hz, 1H), 6.91 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.86 (dddd, J = 9.1, 7.8, 2.9, 1.7 Hz, 1H), 2.61 (tt, J = 11.1, 3.7 Hz, 1H), 2.09 – 2.02 (m, 2H), 1.87 – 1.78 (m, 2H), 1.72 – 1.65 (m, 1H), 1.64 – 1.57 (m, 2H), 1.41 – 1.28 (m, 3H)
¹³C NMR (151 MHz, Chloroform-d)	δ 173.7, 160.1 (dd, J = 246.9, 10.5 Hz), 154.2 (dd, J = 251.8, 12.5 Hz), 134.8 (dd, J = 13.0, 4.0 Hz), 124.3 (dd, J = 9.9, 2.1 Hz), 111.2 (dd, J = 23.0, 3.8 Hz), 105.1 (dd, J = 26.9, 22.4 Hz), 42.9, 29.05, 25.8, 25.4
¹⁹F NMR (565 MHz, CDCl₃)	δ -113.5 (tt, J = 8.2, 5.5 Hz), -124.2 (dddd, J = 10.1, 8.6, 5.5, 1.6 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 263.0854, found: 263.0854

3-fluorophenyl cyclohexanecarboxylate
Identifier	1b
¹H NMR (600 MHz, CDCl₃)	δ 7.32 (td, J = 8.3, 6.5 Hz, 1H), 6.93 (tdd, J = 8.4, 2.5, 0.9 Hz, 1H), 6.88 – 6.85 (m, 1H), 6.84 (dt, J = 9.5, 2.3 Hz, 1H), 2.55 (tt, J = 11.2, 3.7 Hz, 1H), 2.09 – 2.02 (m, 2H), 1.82 (m, 2H), 1.73 – 1.66 (m, 1H), 1.62 – 1.56 (m, 2H), 1.33 (m, 3H)
¹³C NMR (151 MHz, Chloroform-d)	δ 174.2, 163.0 (d, J = 247.4 Hz), 151.9 (d, J = 10.8 Hz), 130.2 (d, J = 9.3 Hz), 117.5 (d, J = 3.3 Hz), 112.7 (d, J = 21.1 Hz), 109.8 (d, J = 24.3 Hz), 43.2, 29.0, 25.8, 25.4
¹⁹F NMR (565 MHz, CDCl₃)	δ -111.7 (ddd, J = 9.2, 8.6, 6.6 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 245.0948, found: 245.0949

4-difluorophenyl cyclohexanecarboxylate
Identifier	1c
¹H NMR (600 MHz, CDCl₃)	δ 7.07 – 7.00 (m, 4H), 2.54 (tt, J = 11.2, 3.7 Hz, 1H), 2.08 – 2.01 (m, 2H), 1.82 (m, 2H), 1.69 (m, 1H), 1.63 – 1.56 (m, 2H), 1.40 – 1.28 (m, 3H)
¹³C NMR (151 MHz, Chloroform-d)	δ 174.7, 160.2 (d, J = 243.8 Hz), 146.8 (d, J = 2.8 Hz), 123.0 (d, J = 8.5 Hz), 116.1 (d, J = 23.3 Hz), 43.2, 29.0, 25.8, 25.4
¹⁹F NMR (565 MHz, CDCl₃)	δ -117.83 (tt, J = 7.9, 4.8 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 245.0948, found: 245.0948

4-(trifluoromethyl)phenyl cyclohexanecarboxylate
Identifier	1d
¹H NMR (600 MHz, CDCl₃)	δ 7.64 (app dd, J = 9.0, 0.6 Hz, 2H), 7.19 (app dd, J = 9.0, 0.7 Hz, 2H), 2.58 (tt, J = 11.2, 3.7 Hz, 1H), 2.10 – 2.03 (m, 2H), 1.83 (m, 2H), 1.74 – 1.67 (m, 1H), 1.63 – 1.56 (m, 2H), 1.41 – 1.27 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.0, 153.5, 128.0, 127.8, 126.7 (q, J = 3.8 Hz), 124.8, 123.0, 122.1, 43.2, 28.9, 25.7, 25.3
¹⁹F NMR (565 MHz, CDCl₃)	δ -62.6 (s)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 295.0916, found: 295.0916

p-tolyl cyclohexanecarboxylate
Identifier	1e
¹H NMR (600 MHz, CDCl₃)	δ 7.10 – 7.07 (m, 2H), 6.88 – 6.84 (m, 2H), 2.47 (tt, J = 11.3, 3.7 Hz, 1H), 2.01 – 1.95 (m, 2H), 1.78 – 1.71 (m, 2H), 1.64 – 1.59 (m, 1H), 1.52 (m, 2H), 1.33 – 1.19 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.8, 148.6, 135.2, 129.9, 121.2, 43.2, 28.97, 25.7, 25.4, 20.9
HRMS (ESI)	m/z calculated for [M+Na]⁺: 241.1199, found: 241.1190

4-methoxyphenyl cyclohexanecarboxylate
Identifier	1f
¹H NMR (600 MHz, CDCl₃)	δ 6.99 – 6.95 (m, 2H), 6.89 – 6.86 (m, 2H), 3.79 (s, 3H), 2.53 (tt, J = 11.3, 3.7 Hz, 1H), 2.05 (m, 2H), 1.85 – 1.78 (m, 2H), 1.71 – 1.66 (m, 1H), 1.62 – 1.55 (m, 2H), 1.39 – 1.27 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.1, 157.3, 144.5, 122.4, 114.6, 55.7, 43.3, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 257.1148, found: 257.1148

3-methoxyphenyl cyclohexanecarboxylate
Identifier	1g
¹H NMR (600 MHz, CDCl₃)	δ 7.26 (app t, J = 8.2 Hz, 1H), 6.77 (ddd, J = 8.3, 2.5, 0.9 Hz, 1H), 6.66 (ddd, J = 8.1, 2.2, 0.9 Hz, 1H), 6.62 (app t, J = 2.3 Hz, 1H), 3.79 (s, 3H), 2.55 (tt, J = 11.3, 3.7 Hz, 1H), 2.09 – 2.03 (m, 2H), 1.86 – 1.78 (m, 2H), 1.72 – 1.66 (m, 1H), 1.64 – 1.54 (m, 2H), 1.41 – 1.26 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.6, 160.6, 152.0, 129.9, 113.9, 111.6, 107.7, 55.5, 43.4, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 257.1148, found: 257.1148

4-butylphenyl cyclohexanecarboxylate
Identifier	1h
¹H NMR (500 MHz, CDCl₃)	δ 7.16 (d, J = 8.4 Hz, 2H), 6.96 (d, J = 8.4 Hz, 2H), 2.63 – 2.50 (m, 3H), 2.11 – 2.01 (m, 2H), 1.86 – 1.77 (m, 2H), 1.68 (m, 1H), 1.59 (m, 4H), 1.40 – 1.27 (m, 9H), 0.88 (t, J = 6.7 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.9, 148.9, 140.4, 129.3, 121.3, 43.4, 35.5, 31.9, 31.6, 29.1, 25.9, 25.5, 22.8, 14.2
HRMS (ESI)	m/z calculated for [M+Na]⁺: 283.1668, found: 283.1669

4-bromophenyl cyclohexanecarboxylate
Identifier	1i
¹H NMR (500 MHz, CDCl₃)	δ 7.50 – 7.46 (m, 4H), 6.98 – 6.93 (m, 4H), 2.54 (tt, J = 11.2, 3.7 Hz, 1H), 2.04 (m, 2H), 1.82 (m, 2H), 1.69 (m, 1H), 1.62 – 1.53 (m, 2H), 1.41 – 1.28 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.4, 150.1, 132.5, 123.5, 118.8, 43.3, 29.1, 25.8, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 305.0147, found: 305.0146

2-isopropylphenyl cyclohexanecarboxylate
Identifier	1j
¹H NMR (500 MHz, CDCl₃)	δ 7.33 – 7.28 (m, 1H), 7.22 – 7.16 (m, 2H), 6.98 – 6.93 (m, 1H), 3.02 (hept, J = 6.9 Hz, 1H), 2.59 (tt, J = 11.3, 3.7 Hz, 1H), 2.09 (m, 2H), 1.87 – 1.80 (m, 2H), 1.74 – 1.68 (m, 1H), 1.62 (m, 2H), 1.43 – 1.27 (m, 4H), 1.20 (d, J = 6.9 Hz, 6H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.8, 148.4, 140.3, 126.7, 126.6, 126.2, 122.4, 43.5, 29.2, 27.4, 25.9, 25.6, 23.1
HRMS (ESI)	m/z calculated for [M+Na]⁺: 269.1512, found: 269.1512

[1,1'-biphenyl]-4-yl cyclohexanecarboxylate
Identifier	1k
¹H NMR (600 MHz, CDCl₃)	δ 7.59 – 7.53 (m, 5H), 7.45 – 7.40 (m, 3H), 7.36 – 7.31 (m, 1H), 7.15 – 7.11 (m, 2H), 2.58 (tt, J = 11.2, 3.7 Hz, 1H), 2.10 – 2.05 (m, 2H), 1.86 – 1.80 (m, , 2H), 1.73 – 1.67 (m, 1H), 1.65 – 1.57 (m, 2H), 1.43 – 1.26 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.7, 150.5, 140.6, 138.9, 128.9, 128.2, 127.4, 127.3, 122.0, 43.4, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 303.1355, found: 303.1356

[1,1'-biphenyl]-2-yl cyclohexanecarboxylate
Identifier	1l
¹H NMR (500 MHz, CDCl₃)	δ 7.51 – 7.35 (m, 7H), 7.18 (d, J = 7.9 Hz, 1H), 2.44 (tt, J = 11.2, 3.6 Hz, 1H), 1.88 (m, 2H), 1.81 – 1.74 (m, 2H), 1.71 – 1.66 (m, 1H), 1.43 (m, 2H), 1.36 – 1.27 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.4, 148.0, 137.6, 135.2, 130.8, 129.1, 128.4, 128.1, 127.4, 126.1, 122.8, 43.1, 28.7, 25.6, 25.3
HRMS (ESI)	m/z calculated for [M+Na]⁺: 303.1355, found: 303.1354

o-tolyl cyclohexanecarboxylate
Identifier	1m
¹H NMR (600 MHz, CDCl₃)	δ 7.23 – 7.17 (m, 2H), 7.13 (td, J = 7.4, 1.3 Hz, 1H), 6.99 – 6.96 (m, 1H), 2.59 (tt, J = 11.3, 3.7 Hz, 1H), 2.17 (s, 3H), 2.10 (m, 2H), 1.84 (m, 2H), 1.74 – 1.67 (m, 1H), 1.62 (m, 2H), 1.42 – 1.27 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.4, 149.6, 131.2, 130.3, 127.0, 126.0, 122.0, 43.4, 29.2, 25.9, 25.6, 16.3
HRMS (ESI)	m/z calculated for [M+Na]⁺: 241.1200, found: 241.1200

2,4-dichlorophenyl cyclohexanecarboxylate
Identifier	1n
¹H NMR (600 MHz, CDCl₃)	δ 7.44 (d, J = 2.4 Hz, 1H), 7.25 (dd, J = 8.6, 2.5 Hz, 1H), 7.05 (d, J = 8.6 Hz, 1H), 2.62 (tt, J = 11.2, 3.7 Hz, 1H), 2.12 – 2.07 (m, 2H), 1.83 (m, 2H), 1.69 (m, 1H), 1.62 (m 2H), 1.41 – 1.30 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 173.5, 146.0, 131.8, 130.2, 128.0, 124.8, 43.2, 29.1, 25.8, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 295.0263, found: 295.0263

benzo[d][1,3]dioxol-5-yl cyclohexanecarboxylate
Identifier	1o
¹H NMR (600 MHz, CDCl₃)	δ 6.78 – 6.74 (m, J = 8.4 Hz, 1H), 6.57 (d, J = 2.3 Hz, 1H), 6.49 (dd, J = 8.4, 2.3 Hz, 1H), 5.97 (s, 2H), 2.52 (tt, J = 11.3, 3.7 Hz, 1H), 2.07 – 2.00 (m, 2H), 1.85 – 1.77 (m, 2H), 1.72 – 1.65 (m, 1H), 1.61 – 1.53 (m, 2H), 1.38 – 1.28 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.0, 148.1, 145.4, 145.3, 114.0, 108.1, 103.9, 101.8, 43.3, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 271.0940, found: 271.0941

4-(tert-butyl)phenyl cyclohexanecarboxylate
Identifier	1p
¹H NMR (500 MHz, CDCl₃)	δ 7.40 – 7.35 (m, 4H), 7.01 – 6.96 (m, 4H), 2.55 (tt, J = 11.2, 3.7 Hz, 1H), 2.10 – 2.02 (m, 2H), 1.86 – 1.79 (m, 2H), 1.68 (m, 1H), 1.65 – 1.53 (m, 2H), 1.37 (m, 2H), 1.32 (s, 9H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.9, 148.7, 148.5, 126.4, 121.0, 43.4, 34.6, 31.6, 29.1, 25.9, 25.3
HRMS (ESI)	m/z calculated for [M+Na]⁺: 283.1668, found: 283.1664

4-chlorophenyl cyclohexanecarboxylate
Identifier	1q
¹H NMR (600 MHz, CDCl₃)	δ 7.35 – 7.31 (m, 2H), 7.03 – 6.98 (m, 2H), 2.55 (tt, J = 11.2, 3.7 Hz, 1H), 2.08 – 2.02 (m, 2H), 1.82 (m, 2H), 1.69 (m 1H), 1.58 (m, 2H), 1.41 – 1.27 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.45, 149.52, 131.10, 129.54, 123.09, 43.29, 29.05, 25.82, 25.47
HRMS (ESI)	m/z calculated for [M+Na]⁺: 261.0652, found: 261.0653

naphthalen-2-yl cyclohexanecarboxylate
Identifier	1r
¹H NMR (600 MHz, CDCl₃)	δ 7.88 – 7.82 (m, 2H), 7.81 – 7.77 (m, 1H), 7.54 (d, J = 2.2 Hz, 1H), 7.51 – 7.43 (m, 2H), 7.21 (dd, J = 8.8, 2.3 Hz, 1H), 2.62 (tt, J = 11.2, 3.7 Hz, 1H), 2.16 – 2.08 (m, 2H), 1.86 (m, 2H), 1.75 – 1.69 (m, 1H), 1.65 (m, 2H), 1.46 – 1.28 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.9, 148.7, 134.0, 131.5, 129.5, 127.9, 127.7, 126.6, 125.7, 121.4, 118.6, 43.4, 29.2, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 217.1199, found: 217.1190

4-(2-phenylpropan-2-yl)phenyl cyclohexanecarboxylate
Identifier	1s
¹H NMR (600 MHz, CDCl₃)	δ 7.24 – 7.20 (m, 2H), 7.19 – 7.15 (m, 4H), 7.14 – 7.10 (m, 1H), 6.93 – 6.89 (m, 2H), 2.49 (tt, J = 11.2, 3.7 Hz, 1H), 2.04 – 1.97 (m, 2H), 1.80 – 1.73 (m, 2H), 1.63 (s, 6H), 1.58 – 1.49 (m, 2H), 1.35 – 1.21 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.8, 150.5, 148.8, 148.1, 128.2, 127.9, 126.9, 125.8, 121.0, 43.3, 42.8, 31.0, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 345.1825, found: 345.1826

4-(benzyloxy)phenyl cyclohexanecarboxylate
Identifier	1t
¹H NMR (500 MHz, CDCl₃)	δ 7.43 – 7.35 (m, 4H), 7.34 – 7.29 (m, 1H), 6.99 – 6.93 (m, 4H), 2.53 (tt, J = 11.2, 3.7 Hz, 1H), 2.07 – 2.00 (m, 2H), 1.85 – 1.77 (m, 2H), 1.71 – 1.64 (m, 1H), 1.63 – 1.52 (m, 2H), 1.41 – 1.26 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.0, 156.5, 144.7, 137.0, 128.7, 128.1, 127.6, 122.5, 115.6, 70.6, 43.3, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 333.1461, found: 333.1461

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl cyclohexanecarboxylate
Identifier	1u
¹H NMR (600 MHz, CDCl₃)	δ 7.83 – 7.80 (m, 2H), 7.08 – 7.05 (m, 2H), 2.58 – 2.52 (m, 1H), 2.06 (m, 2H), 1.85 – 1.78 (m, 2H), 1.68 (m, 1H), 1.59 (m,2H), 1.40 – 1.35 (m, 2H), 1.34 (s, 12H), 1.32 – 1.27 (m, 1H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.4, 153.6, 136.3, 121.1, 84.0, 43.4, 29.1, 25.8, 25.5, 25.0
HRMS (ESI)	m/z calculated for [M+Na]⁺: 353.1900, found: 353.1896

phenyl cyclohexanecarboxylate
Identifier	1v
¹H NMR (300 MHz, CDCl₃)	δ 7.41 – 7.33 (m, 2H), 7.25 – 7.18 (m, 1H), 7.10 – 7.01 (m, 2H), 2.56 (tt, J = 11.2, 3.7 Hz, 1H), 2.13 – 2.02 (m, 2H), 1.89 – 1.77 (m, 2H), 1.67 (m,3H), 1.47 – 1.21 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.5, 149.5, 131.1, 129.5, 123.1, 43.3, 29.1, 25.8, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 227.1042, found: 227.1041

[1,1'-biphenyl]-3-yl cyclohexanecarboxylate
Identifier	1w
¹H NMR (600 MHz, CDCl₃)	δ 7.59 (dt, J = 8.2, 1.6 Hz, 2H), 7.47 – 7.42 (m, 4H), 7.39 – 7.34 (m, 1H), 7.32 – 7.29 (m, 1H), 7.07 (dt, J = 6.8, 2.2 Hz, 1H), 2.60 (tt, J = 11.2, 3.7 Hz, 1H), 2.14 – 2.07 (m, 2H), 1.89 – 1.81 (m, 2H), 1.75 – 1.68 (m, 1H), 1.68 – 1.58 (m, 2H), 1.44 – 1.29 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.7, 151.4, 142.9, 140.4, 129.8, 128.9, 127.8, 127.3, 124.5, 120.5, 120.5, 43.4, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 303.1355, found: 303.1356

6-bromonaphthalen-2-yl cyclohexanecarboxylate
Identifier	1x
Sample qualifier	This product was isolated as a mixture with 40 % of the phenol starting material
¹H NMR (600 MHz, CDCl₃)	δ 8.01 – 7.99 (m, 1H), 7.87 – 7.73 (m, 1H), 7.68 – 7.64 (m, 1H), 7.57 – 7.43 (m, 2H), 7.22 (ddd, J = 14.9, 8.8, 2.3 Hz, 1H), 2.61 (tt, J = 11.2, 3.5 Hz, 1H), 2.10 (m, 2H), 1.89 – 1.80 (m, 2H), 1.75 – 1.69 (m, 1H), 1.68 – 1.59 (m, 2H), 1.44 – 1.30 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.6, 148.8, 133.8, 132.4, 132.2, 129.9, 129.8, 129.3, 129.2, 128.4, 127.8, 127.6, 126.5, 125.6, 122.4, 121.2, 119.5, 118.6, 118.5, 43.3, 29.0, 25.7, 25.4
HRMS (ESI)	m/z calculated for [M+Na]⁺: 355.0304, found: 355.0305

3-hydroxyphenyl cyclohexanecarboxylate
Identifier	1y
¹H NMR (500 MHz, CDCl₃)	δ 7.16 (app.t, J = 8.1 Hz, 1H), 6.62 (dd, J = 8.2, 2.4 Hz, 1H), 6.59 (ddd, J = 8.2, 2.1, 0.6 Hz, 1H), 6.51 (t, J = 2.3 Hz, 1H), 5.90 (bs, J = 8.6 Hz, 1H), 2.55 (tt, J = 11.2, 3.7 Hz, 1H), 2.09 – 1.99 (m, 2H), 1.86 – 1.76 (m, 2H), 1.73 – 1.65 (m, 1H), 1.63 – 1.53 (m, 2H), 1.41 – 1.24 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.4, 156.9, 151.7, 130.1, 113.5, 113.26, 109.4, 43.4, 29.0, 25.8, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 243.0991, found: 243.0991

4-(3-oxobutyl)phenyl cyclohexanecarboxylate
Identifier	1z
¹H NMR (500 MHz, CDCl₃)	δ 7.17 (d, J = 8.5 Hz, 2H), 6.96 (d, J = 8.5 Hz, 2H), 2.88 (t, J = 7.6 Hz, 2H), 2.74 (t, J = 7.6 Hz, 2H), 2.54 (tt, J = 11.2, 3.6 Hz, 1H), 2.14 (s, 3H), 2.09 – 2.00 (m, 2H), 1.85 – 1.78 (m, 2H), 1.71 – 1.65 (m , 1H), 1.64 – 1.52 (m, 2H), 1.42 – 1.23 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 207.9, 174.8, 149.3, 138.5, 129.3, 121.7, 45.3, 43.3, 30.2, 29.2, 29.1, 25.9, 25.5
HRMS (ESI)	m/z calculated for [M+Na]⁺: 297.1461, found: 297.1462

2,4-difluorophenyl 3,3-dimethylbutanoate
Identifier	1aa
¹H NMR (600 MHz, CDCl₃)	δ 7.08 (td, 1H), 6.92 (ddd, J = 10.1, 8.4, 2.8 Hz, 1H), 6.86 (dddd, J = 9.0, 7.8, 2.9, 1.7 Hz, 1H), 2.47 (s, 2H), 1.13 (s, H)
¹³C NMR (151 MHz, Chloroform-d)	δ 169.5, 160.0 (dd, J = 247.1, 10.5 Hz), 154.1 (dd, J = 251.8, 12.5 Hz), 134.3 (dd, J = 13.1, 4.0 Hz), 124.3 (dd, J = 9.9, 2.3 Hz), 111.1 (dd, J = 23.0, 3.9 Hz), 105.0 (dd, J = 26.9, 22.5 Hz), 47.3, 29.5
¹⁹F NMR (565 MHz, Chloroform-d)	δ -113.3 (tt, J = 8.1, 5.6 Hz), -123.1 (dddd, J = 10.2, 8.5, 5.7, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 251.0854, found: 251.0855

2,4-difluorophenyl nonanoate
Identifier	1ab
¹H NMR (600 MHz, CDCl₃)	δ 7.08 (td, J = 8.7, 5.5 Hz, 1H), 6.94 – 6.90 (m, 1H), 6.86 (dddd, J = 9.0, 7.8, 2.9, 1.7 Hz, 1H), 2.58 (t, J = 7.5 Hz, 2H), 1.76 (app dt, J = 15.2, 7.5 Hz, 2H), 1.41 (m, 2H), 1.36 – 1.27 (m, 8H), 0.89 (t, J = 7.1 Hz, 3H)
¹³C NMR (151 MHz, Chloroform-d)	δ 171.4, 160.2 (dd, J = 247.0, 10.4 Hz), 154.2 (dd, J = 251.8, 12.5 Hz), 134.6 (dd, J = 13.0, 4.0 Hz), 124.3 (dd, J = 10.0, 2.1 Hz), 111.3 (dd, J = 23.0, 3.8 Hz), 105.2 (dd, J = 26.9, 22.5 Hz), 33.9, 31.9, 29.3 – 29.0 (m), 25.0, 22.7, 14.2
¹⁹F NMR (565 MHz, CDCl₃)	δ -112.9 (tt, J = 8.1, 5.5 Hz), -123.5 (dddd, J = 10.1, 8.5, 5.6, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 293.1323, found: 293.13225

2,4-difluorophenyl pentanoate
Identifier	1ac
¹H NMR (600 MHz, CDCl₃)	δ 7.08 (td, J = 8.7, 5.5 Hz, 1H), 6.92 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.89 – 6.83 (m, 1H), 2.59 (t, J = 7.5 Hz, 2H), 1.79 – 1.71 (m, 2H), 1.49 – 1.41 (m, 2H), 0.97 (t, J = 7.4 Hz, 3H)
¹³C NMR (151 MHz, Chloroform-d)	δ 171.4, 160.2 (dd, J = 247.0, 10.5 Hz), 154.2 (dd, J = 251.8, 12.5 Hz), 134.6 (dd, J = 13.0, 4.0 Hz), 124.3 (dd, J = 9.9, 2.1 Hz), 111.3 (dd, J = 23.0, 3.9 Hz), 105.2 (dd, J = 26.9, 22.5 Hz), 33.6, 27.1, 22.3, 13.8
¹⁹F NMR (565 MHz, CDCl₃)	δ -112.9 (tt, J = 8.1, 5.5 Hz), -123.5 (dddd, J = 10.2, 8.5, 5.6, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 237.0697, found: 237.0698

2,4-difluorophenyl 3-cyclohexylpropanoate
Identifier	1ad
¹H NMR (500 MHz, CDCl₃)	δ 7.08 (td, J = 8.7, 5.5 Hz, 1H), 6.91 (ddd, J = 10.0, 8.5, 2.9 Hz, 1H), 6.86 (m, 1H), 2.62 – 2.57 (m, 2H), 1.74 (m, 4H), 1.66 (dd, J = 15.1, 7.2 Hz, 3H), 1.37 – 1.28 (m, 1H), 1.25 – 1.10 (m, 3H), 0.99 – 0.90 (m, 2H)
¹³C NMR (126 MHz, Chloroform-d)	δ 171.7, 160.2 (dd, J = 247.0, 10.5 Hz), 154.2 (dd, J = 251.8, 12.5 Hz), 134.6 (dd, J = 13.0, 4.0 Hz), 124.3, 111.3 (dd, J = 23.0, 3.8 Hz), 105.2 (dd, J = 26.9, 22.5 Hz), 37.3, 33.1, 32.3, 31.5, 26.6, 26.3
¹⁹F NMR (471 MHz, Chloroform-d)	δ -113.4 (tt, J = 8.2, 5.5 Hz), -124.0 (m)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 291.1167, found: 291.1167

2,4-difluorophenyl cyclopentanecarboxylate
Identifier	1ae
¹H NMR (500 MHz, CDCl₃)	δ 7.08 (dt, J = 8.7, 5.5 Hz, 1H), 6.91 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.88 – 6.83 (m, 1H), 3.07 – 2.97 (m, 1H), 2.08 – 1.93 (m, 4H), 1.82 – 1.74 (m, 2H), 1.72 – 1.62 (m, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.3, 160.0 (dd, J = 246.9, 10.5 Hz), 154.1 (dd, J = 251.6, 12.5 Hz), 134.7 (dd, J = 13.0, 4.1 Hz), 124.2 (dd, J = 9.9, 2.2 Hz), 111.1 (dd, J = 23.0, 3.9 Hz), 105.0 (dd, J = 26.9, 22.4 Hz), 43.4, 30.1, 25.9
¹⁹F NMR (471 MHz, CDCl₃)	δ -113.5 – -113.6 (m), -124.32 (d, J = 5.5 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 249.0697, found: 249.0697

2,4-difluorophenyl 2-methylbutanoate
Identifier	1af
¹H NMR (600 MHz, CDCl₃)	δ 7.07 (td, J = 8.7, 5.5 Hz, 1H), 6.92 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.86 (dddd, J = 9.0, 7.8, 2.9, 1.7 Hz, 1H), 2.67 (sext, 1H), 1.89 – 1.78 (dq, 1H), 1.69 – 1.59 (m, 1H), 1.30 (d, J = 7.0 Hz, 3H), 1.02 (t, J = 7.5 Hz, 3H)
¹³C NMR (151 MHz, Chloroform-d)	δ 174.3, 160.2 (dd, J = 247.0, 10.5 Hz), 154.2 (dd, J = 251.7, 12.5 Hz), 134.7 (dd, J = 13.0, 4.1 Hz), 124.3 (dd, J = 9.9, 2.2 Hz), 111.3 (dd, J = 23.0, 3.9 Hz), 105.2 (dd, J = 26.9, 22.4 Hz), 41.0, 26.8, 16.7, 11.6
¹⁹F NMR (565 MHz, CDCl₃)	δ -113.0 (tt, J = 8.1, 5.5 Hz), -123.6 (dddd, J = 10.1, 8.5, 5.6, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 237.0697, found: 237.0699

2,4-difluorophenyl cycloheptanecarboxylate
Identifier	1ag
¹H NMR (600 MHz, CDCl₃)	δ 7.33 (s, 1H), 7.32 – 7.32 (m, 1H), 7.28 – 7.26 (m, 2H), 7.26 – 7.24 (m, 1H), 7.09 – 7.03 (m, 3H), 6.91 (ddd, J = 10.0, 8.4, 2.8 Hz, 1H), 6.86 (dddd, J = 7.8, 5.7, 2.9, 1.7 Hz, 3H), 3.53 (s, 6H), 2.91 (app d, J = 11.6 Hz, 6H), 2.61 (tt, J = 10.9, 4.1 Hz, 3H), 2.13 (app t, J = 10.9 Hz, 6H), 2.08 – 2.00 (m, 7H), 1.93 (ddd, J = 24.5, 11.1, 3.7 Hz, 7H)
¹³C NMR (151 MHz, Chloroform-d)	δ 172.7, 160.0 (dd, J = 247.0, 10.3 Hz), 154.0 (dd, J = 251.7, 12.6 Hz), 134.5 (dd, J = 13.0, 4.1 Hz), 129.13, 128.2, 127.0, 124.1 (dd, J = 9.8, 2.0 Hz), 111.1 (dd, J = 22.9, 3.8 Hz), 105.0 (dd, J = 26.9, 22.3 Hz), 63.1, 52.6, 40.7, 28.1
¹⁹F NMR (565 MHz, CDCl₃)	δ -112.7 – -114.4 (m), -124.2 (dd, J = 14.3, 8.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 277.1010, found: 277.1011

2,4-difluorophenyl (1S,4R)-bicyclo[2.2.1]heptane-2-carboxylate
Identifier	1ah
¹H NMR (600 MHz, CDCl₃)	δ 7.07 (td, J = 8.8, 5.5 Hz, 1H), 6.91 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.86 (dddd, J = 9.4, 7.8, 2.9, 1.7 Hz, 1H), 2.70 (app d, J = 4.1 Hz, 1H), 2.62 (dd, J = 8.9, 5.1 Hz, 1H), 2.37 (app t, J = 4.0 Hz, 1H), 2.01 – 1.92 (m, 1H), 1.67 – 1.48 (m, 5H), 1.37 – 1.30 (m, 1H), 1.27 – 1.22 (m, 2H)
¹³C NMR (151 MHz, Chloroform-d)	δ 173.7, 160.1 (dd, J = 246.9, 10.5 Hz), 154.2 (dd, J = 251.6, 12.5 Hz), 134.9 (dd, J = 13.0, 4.0 Hz), 124.3 (dd, J = 9.9, 2.2 Hz), 111.2 (dd, J = 23.0, 3.9 Hz), 105.1 (dd, J = 26.9, 22.4 Hz), 46.3, 41.3, 36.6, 36.2, 34.3, 29.5, 28.7
¹⁹F NMR (565 MHz, Chloroform-d)	δ -113.5 (tt, J = 8.2, 5.5 Hz), -124.2 (dddd, J = 10.1, 8.5, 5.5, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 275.0854, found: 275.0855

2,4-difluorophenyl 2,3-dihydro-1H-indene-2-carboxylate
Identifier	1ai
¹H NMR (500 MHz, CDCl₃)	δ 7.25 (t, J = 4.3 Hz, 2H), 7.23 – 7.18 (m, 1H), 7.11 (td, J = 8.7, 5.5 Hz, 1H), 6.92 (ddd, J = 10.1, 8.5, 2.9 Hz, 1H), 6.89 – 6.84 (m, 1H), 3.67 – 3.57 (m, 1H), 3.43 (dd, J = 15.9, 8.0 Hz, 2H), 3.37 (dd, J = 15.8, 9.3 Hz, 2H)
¹³C NMR (126 MHz, Chloroform-d)	δ 173.0, 160.2 (dd, J = 247.3, 10.4 Hz), 154.2 (dd, J = 251.9, 12.5 Hz), 141.2, 134.7 (dd, J = 13.0, 4.0 Hz), 126.9, 124.5, 124.3 (dd, J = 9.9, 2.0 Hz), 111.3 (dd, J = 23.0, 3.8 Hz), 105.2 (dd, J = 27.0, 22.4 Hz), 43.3, 36.3
¹⁹F NMR (471 MHz, Chloroform-d)	δ -113.1 (tt, J = 8.2, 5.6 Hz), -124.2 (dddd, J = 10.1, 7.5, 5.6, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 297.0697, found: 297.0698

2,4-difluorophenyl pivalate
Identifier	1aj
¹H NMR (600 MHz, CDCl₃)	δ 7.06 (td, J = 8.8, 5.5 Hz, 2H), 6.91 (ddd, J = 10.1, 8.4, 2.9 Hz, 2H), 6.88 – 6.84 (m, 1H), 1.37 (s, 16H)
¹³C NMR (151 MHz, Chloroform-d)	δ 176.3, 160.1 (dd, J = 246.8, 10.4 Hz), 154.2 (dd, J = 251.6, 12.5 Hz), 135.0 (dd, J = 13.0, 4.0 Hz), 124.3 (dd, J = 9.9, 2.1 Hz), 111.2 (dd, J = 23.0, 3.9 Hz), 105.1 (dd, J = 26.9, 22.4 Hz), 39.3, 27.2
¹⁹F NMR (565 MHz, CDCl₃)	δ -113.1 (m), -124.1 (dd, J = 5.5, 1.6 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 237.0697, found: 237.0697

2,4-difluorophenyl (3r,5r,7r)-adamantane-1-carboxylate
Identifier	1ak
¹H NMR (600 MHz, CDCl₃)	δ 7.05 (td, J = 8.8, 5.5 Hz, 1H), 6.90 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.87 – 6.82 (m, 1H), 2.08 (m, 3H), 2.06 (m, 6H), 1.77 (m, 6H)
¹³C NMR (151 MHz, Chloroform-d)	δ 175.2, 159.9 (dd, J = 246.7, 10.4 Hz), 154.0 (dd, J = 251.5, 12.5 Hz), 134.8 (dd, J = 13.0, 4.0 Hz), 124.2 (dd, J = 10.0, 2.2 Hz), 111.0 (dd, J = 23.0, 3.8 Hz), 105.0 (dd, J = 26.9, 22.4 Hz), 41.1, 38.7, 36.5, 36.3, 35.8, 27.8, 27.3
¹⁹F NMR (565 MHz, CDCl₃)	δ -113.7 (tt, J = 8.1, 5.5 Hz), -124.4 (dddd, J = 10.1, 8.6, 5.4, 1.6 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 315.1167, found: 315.1168

2,4-difluorophenyl 2-methoxycyclohexane-1-carboxylate
Identifier	1al
Sample qualifier	The product is isolated as a mixture of diastereomers in a ratio of (1:1) with overlapping signals
¹H NMR (400 MHz, CDCl₃)	δ 7.10 (td, J = 8.7, 5.5 Hz, 1H), 6.95 – 6.80 (m, 2H), 3.48 (td, J = 10.2, 4.1 Hz, 1H), 3.40 (s, 3H), 2.62 (ddd, J = 12.0, 9.9, 3.9 Hz, 1H), 2.22 (m, 1H), 2.17 – 2.09 (m, 1H), 1.88 – 1.81 (m, 1H), 1.80 – 1.71 (m, 1H), 1.68 – 1.59 (m, 1H), 1.36 – 1.26 (m, 3H)
¹³C NMR (126 MHz, Chloroform-d)	δ 172.5, 160.0 (dd, J = 246.9, 10.4 Hz), 154.0 (dd, J = 252.0, 12.6 Hz), 134.5 (dd, J = 13.1, 4.0 Hz), 132.2 (d, J = 10.8 Hz), 128.4 (d, J = 12.6 Hz), 124.3 (dd, J = 9.9, 2.1 Hz), 111.1 (dd, J = 23.0, 3.9 Hz), 105.0 (dd, J = 26.9, 22.4 Hz), 79.9, 56.6, 50.0, 29.7, 28.6, 24.6, 23.8
¹⁹F NMR (471 MHz, CDCl₃)	δ -113.3 – -113.6 (m), -124.0 – -124.3 (m)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 293.0959, found: 293.0959

2,4-difluorophenyl 1-benzylpiperidine-4-carboxylate
Identifier	1am
¹H NMR (600 MHz, CDCl₃)	δ 7.06 (td, J = 8.8, 5.5 Hz, 1H), 6.91 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.86 (dddd, J = 9.3, 7.8, 2.9, 1.7 Hz, 1H), 2.83 – 2.74 (m, 1H), 2.14 – 2.04 (m, 2H), 1.88 – 1.75 (m, 4H), 1.67 – 1.54 (m, 6H)
¹³C NMR (151 MHz, Chloroform-d)	δ 174.6, 160.1 (dd, J = 246.9, 10.5 Hz), 154.2 (dd, J = 251.6, 12.5 Hz), 134.8 (dd, J = 13.0, 4.0 Hz), 124.3 (dd, J = 9.9, 2.2 Hz), 111.2 (dd, J = 23.0, 3.9 Hz), 105.1 (dd, J = 26.9, 22.4 Hz), 44.7, 30.8, 28.4, 26.4
¹⁹F NMR (565 MHz, CDCl₃)	δ -113.5 (tt, J = 8.1, 5.5 Hz), -124.3 (dddd, J = 10.1, 8.6, 5.5, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 354.1276, found: 354.1276

2,4-difluorophenyl 4-oxocyclohexane-1-carboxylate
Identifier	1an
¹H NMR (500 MHz, CDCl₃)	δ 7.10 (td, J = 8.7, 5.5 Hz, 1H), 6.98 – 6.83 (m, 2H), 3.12 – 3.00 (m, 1H), 2.57 (app dt, J = 14.6, 5.6 Hz, 2H), 2.47 – 2.31 (m, 4H), 2.28 – 2.14 (m, 2H)
¹³C NMR (126 MHz, Chloroform-d)	δ 209.4, 171.9, 160.3 (dd, J = 247.7, 10.5 Hz), 154.0(dd, J = 251.6, 12.5 Hz), 134.4 (dd, J = 13.1, 4.0 Hz), 124.2 (dd, J = 9.9, 1.9 Hz), 111.4 (dd, J = 23.1, 3.9 Hz), 105.3 (dd, J = 27.0, 22.3 Hz), 40.4, 39.5, 28.5
¹⁹F NMR (471 MHz, CDCl₃)	δ -112.7 (dq, J = 8.1, 5.6 Hz), -122.4 – -125.7 (m)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 277.0646, found: 277.0647

2,4-difluorophenyl 4-phenylbutanoate
Identifier	1ao
¹H NMR (500 MHz, CDCl₃)	δ 7.34 – 7.28 (m, 2H), 7.25 – 7.19 (m, 3H), 7.07 (td, J = 8.7, 5.5 Hz, 1H), 6.92 (ddd, J = 10.1, 8.5, 2.9 Hz, 1H), 6.89 – 6.83 (m, 1H), 2.75 (t, J = 7.6 Hz, 2H), 2.61 (t, J = 7.4 Hz, 2H), 2.13 – 2.06 (m, 2H)
¹³C NMR (126 MHz, Chloroform-d)	δ 171.0, 160.2 (dd, J = 247.2, 10.5 Hz), 154.2 (dd, J = 251.7, 12.6 Hz), 141.1, 134.6 (d, J = 8.9 Hz), 128.6 (d, J = 4.8 Hz), 126.2, 124.3 (dd, J = 9.9, 2.1 Hz), 111.3 (dd, J = 23.0, 3.8 Hz), 105.2 (dd, J = 26.9, 22.4 Hz), 35.0, 33.1, 29.8, 26.6
¹⁹F NMR (471 MHz, CDCl₃)	δ -113.2 (ddd, J = 16.1, 8.0, 5.6 Hz), -123.9 (ddd, J = 10.0, 5.7, 1.4 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 299.0854, found: 299.0854

2,4-difluorophenyl 4-(tert-butyl)cyclohexane-1-carboxylate
Identifier	1ap
Sample qualifier	The product was obtained as a mixture of diastereomers (d.r 3:2)
¹H NMR (500 MHz, CDCl₃)	δ 7.06 (td, J = 8.7, 5.6 Hz, 1H), 6.95 – 6.82 (m, 2H), 2.94 (s, 1H), 2.49 (tt, J = 12.3, 3.6 Hz, 1H), 2.35 (d, J = 13.6 Hz, 1H), 2.19 (d, J = 12.8 Hz, 1H), 2.05 – 1.80 (m, 2H), 1.71 (d, J = 12.5 Hz, 1H), 1.61 – 1.49 (m, 3H), 1.34 – 1.19 (m, 2H), 1.14 – 1.00 (m, 2H), 0.87 (s, 5H), 0.85 (s, 4H)
¹³C NMR (126 MHz, Chloroform-d)	δ 173.8, 172.9, 160.1 (dd, J = 247.0, 10.5 Hz), 154.2 (ddd, J = 251.8, 12.7, 7.8 Hz), 134.8 (dd, J = 13.0, 4.0 Hz), 124.4 (dd, J = 9.9, 2.1 Hz), 111.2 (dt, J = 23.0, 4.5 Hz), 105.1 (ddd, J = 26.8, 22.4, 2.4 Hz), 47.9, 47.4, 43.3, 39.1, 32.6 (d, J = 14.1 Hz), 29.6, 28.1, 27.7 – 26.9 (m), 26.63, 23.7
¹⁹F NMR (471 MHz, Chloroform-d)	δ -113.6 (dtt, J = 22.0, 8.1, 5.5 Hz), -123.7 (ddt, J = 10.0, 7.5, 3.5 Hz), -124.3 – -124.4 (m)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 319.1480, found: 319.1481

2,4-difluorophenyl 6-(4-bromophenyl)tetrahydro-2H-pyran-3-carboxylate
Identifier	1aq
Sample qualifier	The product was obtained as a mixture of diastereomers (d.r 3:1)
¹H NMR (400 MHz, CDCl₃)	δ 7.51 – 7.45 (m, 3H), 7.28 – 7.22 (m, 3H), 7.17 – 7.11 (m, 1H), 7.07 (td, J = 8.6, 5.4 Hz, 1H), 7.00 – 6.84 (m, 3H), 4.63 (dd, J = 11.1, 2.2 Hz, 1H), 4.38 (dd, J = 11.4, 2.1 Hz, 1H), 4.28 (ddd, J = 11.8, 4.6, 1.7 Hz, 1H), 4.07 (dd, J = 12.4, 2.8 Hz, 1H), 3.87 (td, J = 12.1, 2.5 Hz, 1H), 3.73 – 3.64 (m, 1H), 3.26 – 3.20 (m, 1H), 3.02 (tt, J = 12.2, 3.9 Hz, 1H), 2.37 (ddd, J = 13.9, 4.6, 2.3 Hz, 1H), 2.27 (ddt, J = 13.4, 3.9, 2.0 Hz, 1H), 2.23 – 2.15 (m, 1H), 2.12 – 2.04 (m, 1H), 2.04 – 1.95 (m, 1H), 1.94 – 1.90 (m, 1H), 1.88 (dd, J = 10.0, 4.0 Hz, 1H), 1.80 (ddd, J = 13.3, 12.3, 11.5 Hz, 1H)
¹³C NMR (101 MHz, CDCl₃)	δ 171.7, 141.1, 131.6 (d, J = 5.2 Hz), 127.6 (d, J = 6.1 Hz), 124.2 (d, J = 11.7 Hz), 121.7, 111.4 (dd, J = 23.1, 3.9 Hz), 105.3 (dd, J = 27.0, 22.3 Hz), 78.4, 75.5, 67.6, 65.2, 40.9, 37.4, 36.0, 29.8, 28.1
¹⁹F NMR (471 MHz, Chloroform-d)	δ -112.6 (tt, J = 8.1, 5.6 Hz), -112.8 (tt, J = 8.1, 5.6 Hz), -124.1 (dddd, J = 10.2, 8.0, 5.6, 1.7 Hz), -124.3 (dddd, J = 10.2, 7.7, 5.7, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 419.0064, found: 419.0065

2,4-difluorophenyl tetrahydro-2H-pyran-4-carboxylate
Identifier	1ar
¹H NMR (600 MHz, CDCl₃)	δ 7.08 (td, J = 8.8, 5.5 Hz, 1H), 6.92 (ddd, J = 10.1, 8.4, 2.9 Hz, 1H), 6.87 (dddd, J = 9.0, 7.8, 2.9, 1.7 Hz, 1H), 4.02 (dt, J = 11.7, 3.8 Hz, 2H), 3.51 (ddd, J = 11.7, 10.8, 2.7 Hz, 2H), 2.86 (tt, J = 10.7, 4.3 Hz, 1H), 2.06 – 1.86 (m, 4H)
¹³C NMR (151 MHz, Chloroform-d)	δ 172.1, 160.2 (dd, J = 247.4, 10.5 Hz), 154.1 (dd, J = 251.7, 12.5 Hz), 134.5 (dd, J = 13.0, 4.0 Hz), 124.2 (dd, J = 9.9, 2.0 Hz), 111.3 (dd, J = 23.0, 3.9 Hz), 105.2 (dd, J = 27.0, 22.4 Hz), 67.0, 39.9, 28.6
¹⁹F NMR (376 MHz, CDCl₃)	δ -113.6 (d, J = 5.5 Hz), -124.3 (d, J = 5.5 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 265.0646, found: 265.0647

1-(tert-butyl) 4-(2,4-difluorophenyl) piperidine-1,4-dicarboxylate
Identifier	1as
¹H NMR (400 MHz, CDCl₃)	δ 7.07 (td, J = 8.7, 5.5 Hz, 1H), 6.96 – 6.83 (m, 2H), 4.05 (p.d, J = 8.5 Hz, 2H), 2.95 (app t, J = 12.5 Hz, 2H), 2.77 (tt, J = 10.7, 4.0 Hz, 1H), 2.03 (app dd, J = 12.6, 3.3 Hz, 2H), 1.79 (dtd, J = 13.6, 11.0, 4.2 Hz, 2H), 1.47 (s, 9H)
¹³C NMR (101 MHz, Chloroform-d)	δ 172.2, 160.3 (dd, J = 247.6, 10.5 Hz), 158.2 (d, J = 13.8 Hz), 154.8, 134.5 (dd, J = 13.0, 4.1 Hz), 124.2 (dd, J = 9.9, 2.0 Hz), 111.4 (dd, J = 23.1, 3.9 Hz), 105.2 (dd, J = 27.0, 22.3 Hz), 79.9, 40.9, 28.5, 28.0
¹⁹F NMR (376 MHz, CDCl₃)	δ -113.0 (d, J = 5.7 Hz), -124.3 (d, J = 5.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 364.1330, found: 364.1335

2,4-difluorophenyl 1-(pyrimidin-2-yl)piperidine-4-carboxylate
Identifier	1at
¹H NMR (600 MHz, CDCl₃)	δ 8.31 (d, J = 4.7 Hz, 2H), 7.08 (td, J = 8.7, 5.5 Hz, 1H), 6.92 (ddd, J = 10.1, 8.4, 2.9 Hz, 2H), 6.89 – 6.84 (m, 2H), 6.48 (t, J = 4.7 Hz, 1H), 4.68 (dt, J = 13.6, 3.5 Hz, 2H), 3.23 – 3.13 (m, 2H), 2.90 (tt, J = 10.8, 4.0 Hz, 1H), 2.14 (ddd, J = 8.7, 6.7, 3.3 Hz, 2H), 1.87 (dtd, J = 13.6, 11.1, 4.1 Hz, 1H)
¹³C NMR (151 MHz, Chloroform-d)	δ 172.4, 161.6, 160.2 (dd, J = 247.3, 10.5 Hz), 157.9, 154.1 (dd, J = 251.8, 12.5 Hz), 134.6 (dd, J = 13.0, 4.0 Hz), 124.2 (dd, J = 9.9, 2.0 Hz), 111.3 (dd, J = 23.0, 3.9 Hz), 109.9, 105.2 (dd, J = 27.0, 22.4 Hz), 43.1, 41.3, 27.9
¹⁹F NMR (565 MHz, CDCl₃)	δ -112.6 (tt, J = 8.1, 5.6 Hz), -123.7 (dddd, J = 10.1, 8.5, 5.6, 1.7 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 342.1024, found: 342.1025

2,4-difluorophenyl 1,4-dioxaspiro[4.5]decane-8-carboxylate
Identifier	1au
¹H NMR (500 MHz, CDCl₃)	δ 7.06 (td, J = 8.7, 5.5 Hz, 1H), 6.91 (ddd, J = 10.1, 8.5, 2.9 Hz, 1H), 6.88 – 6.83 (m, 1H), 3.96 (s, 4H), 2.66 (tt, J = 10.4, 3.9 Hz, 2H), 2.14 – 2.06 (m, 2H), 1.97 (dt, J = 13.7, 5.8 Hz, 2H), 1.90 – 1.80 (m, 2H), 1.67 – 1.59 (m, 2H)
¹³C NMR (126 MHz, Chloroform-d)	δ 172.8, 160.2 (dd, J = 247.1, 10.5 Hz), 154.1 (dd, J = 251.8, 12.6 Hz), 134.7 (dd, J = 13.0, 4.0 Hz), 124.3 (dd, J = 9.9, 2.0 Hz), 111.3 (dd, J = 23.0, 3.9 Hz), 108.0, 105. (dd, J = 26.9, 22.4 Hz), 64.5 (d, J = 3.9 Hz), 41.3, 33.7, 26.3
¹⁹F NMR (471 MHz, CDCl₃)	δ -113.3 (dq, J = 8.0, 5.6 Hz), -123.8 – -125.1 (m)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 321.0908, found: 321.0909

2,4-difluorophenyl 3-(4-isobutylphenyl)butanoate
Identifier	1av
¹H NMR (500 MHz, CDCl₃)	δ 7.18 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), 6.94 – 6.75 (m, 3H), 3.42 – 3.32 (sext, 2H), 2.85 (ddd, J = 23.2, 15.1, 7.6 Hz, 2H), 2.46 (d, J = 7.2 Hz, 2H), 1.86 (h, J = 13.3, 6.7 Hz, 1H), 1.40 (d, J = 7.0 Hz, 3H), 0.91 (d, J = 6.6 Hz, 7H)
¹³C NMR (126 MHz, Chloroform-d)	δ 170.0, 160.2 (dd, J = 247.1, 10.3 Hz), 154.1 (dd, J = 252.0, 12.5 Hz), 142.4, 140.1, 134.5 (dd, J = 13.1, 4.1 Hz), 129.4, 129.1 (d, J = 4.9 Hz), 126.6 (dd, J = 5.9, 1.8 Hz), 126.2, 125.3, 124.3 (dd, J = 9.9, 2.1 Hz), 111.2 (dd, J = 23.0, 3.8 Hz), 105.1 (dd, J = 26.9, 22.4 Hz), 45.1, 42.6, 36.4, 30.3, 22.5, 21.9
¹⁹F NMR (471 MHz, Chloroform-d)	δ -113.3 (tt, J = 8.2, 5.6 Hz), -123.8 (dddd, J = 10.0, 8.3, 5.6, 1.4 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 355.1480, found: 355.1480

2,4-difluorophenyl 3-(6-methoxynaphthalen-2-yl)butanoate
Identifier	1aw
¹H NMR (400 MHz, CDCl₃)	δ 7.76 – 7.68 (m, 3H), 7.64 (app d, J = 1.5 Hz, 1H), 7.55 – 7.42 (m, 1H), 7.39 (dd, J = 8.5, 1.8 Hz, 1H), 7.17 – 7.10 (m, 2H), 6.91 – 6.82 (m, 2H), 6.78 (dddd, J = 9.1, 7.8, 2.8, 1.4 Hz, 1H), 3.92 (s, 3H), 3.59 – 3.48 (m, 1H), 2.94 (ddd, J = 23.2, 15.2, 7.6 Hz, 2H), 1.48 (d, J = 7.0 Hz, 3H)
¹³C NMR (126 MHz, Chloroform-d)	δ 170.0, 161.4 – 158.4 (m), 157.64, 154.1 (dd, J = 252.1, 12.4 Hz), 140.3, 134.4 (dd, J = 13.1, 4.0 Hz), 133.6, 133.4, 132.7, 132.4 (d, J = 10.7 Hz), 131.6 (d, J = 2.9 Hz), 129.2 (d, J = 17.1 Hz), 128.6 (d, J = 12.5 Hz), 127.3, 125.97, 125.1, 124.3 (dd, J = 9.9, 2.0 Hz), 119.0, 111.3 (dd, J = 23.0, 3.9 Hz), 105.8, 105.1 (dd, J = 26.9, 22.4 Hz), 55.4, 42.6, 36.7, 21.9
¹⁹F NMR (471 MHz, Chloroform-d)	δ -113.2 (tt, J = 8.2, 5.6 Hz), -123.8 (dddd, J = 10.1, 8.4, 5.7, 1.6 Hz)
HRMS (ESI)	m/z calculated for [M+Na]⁺: 379.1116, found: 379.1117

N-cyclopentylcyclohexanecarboxamide
Identifier	2a
¹H NMR (500 MHz, CDCl₃)	δ 5.40 (bs, 1H), 4.19 (dt, J = 13.9, 6.9 Hz, 1H), 2.06 – 1.91 (m, 3H), 1.86 – 1.72 (m, 5H), 1.67 – 1.54 (m, 5H), 1.46 – 1.26 (m, 6H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.8, 51.0, 45.8, 33.4, 29.9, 25.9, 23.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 196.1695, found: 196.1696

cyclohexyl(4-phenylpiperazin-1-yl)methanone
Identifier	2b
¹H NMR (600 MHz, CDCl₃)	δ 7.30 – 7.25 (m, 2H), 6.94 – 6.86 (m, 3H), 3.80 – 3.60 (m, 4H), 3.21 – 3.10 (m, 4H), 2.51 (tt, J = 11.6, 3.4 Hz, 1H), 1.85 – 1.79 (m, 2H), 1.78 – 1.72 (m, 2H), 1.71 – 1.67 (m, 1H), 1.55 (qd, J = 12.4, 3.0 Hz, 2H), 1.36 – 1.12 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.5, 150.9, 129.1, 120.4, 116.5, 49.9, 49.4, 45.2, 41.4, 40.3, 29.3, 25.8, 25.8
HRMS (ESI)	m/z calculated for [M+H]⁺: 273.1961, found: 273.1962

cyclohexyl(3,4-dihydroisoquinolin-2(1H)-yl)methanone
Identifier	2c
Sample qualifier	The product was obtained as a mixture of rotamers
¹H NMR (500 MHz, CDCl₃)	δ 7.22 – 7.07 (m, 4H), 4.69 (d, J = 31.4 Hz, 2H), 3.77 (dt, J = 52.0, 5.9 Hz, 2H), 2.87 (dt, J = 35.6, 5.7 Hz, 2H), 2.61 – 2.50 (m, 1H), 1.87 – 1.66 (m, 5H), 1.62 – 1.49 (m, 2H), 1.36 – 1.26 (m, 3H)
¹³C NMR (126 MHz, Chloroform-d)	δ 175.0, 174.8, 135.2, 134.0, 133.7, 132.8, 128.9, 128.2, 126.8, 126.6, 126.4, 126.3, 126.2, 125.9, 47.2, 44.3, 42.9, 41.0, 40.9, 39.7, 29.8, 29.3, 29.2, 28.4, 25.8, 25.8
HRMS (ESI)	m/z calculated for [M+H]⁺: 244.1695, found: 244.1695

N-benzylcyclohexanecarboxamide
Identifier	2d
¹H NMR (600 MHz, CDCl₃)	δ 7.28 – 7.21 (m, 2H), 7.21 – 7.13 (m, 3H), 5.76 (s, 1H), 4.35 (d, J = 5.7 Hz, 2H), 2.04 (tt, J = 11.8, 3.5 Hz, 1H), 1.84 – 1.78 (m, 2H), 1.75 – 1.68 (m, 2H), 1.62 – 1.56 (m, 1H), 1.44 – 1.34 (m, 2H), 1.26 – 1.10 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 176.1, 138.7, 128.8, 127.8, 127.5, 45.7, 43.5, 29.8, 25.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 218.1539, found: 218.1540

N-(4-(tert-butyl)benzyl)cyclohexanecarboxamide
Identifier	2e
¹H NMR (600 MHz, CDCl₃)	δ 7.36 – 7.33 (m, 2H), 7.21 – 7.18 (m, 2H), 5.82 (s, 1H), 4.39 (d, J = 5.6 Hz, 2H), 2.10 (tt, J = 11.8, 3.5 Hz, 1H), 1.91 – 1.85 (m, 2H), 1.81 – 1.75 (m, 2H), 1.69 – 1.63 (m, 1H), 1.51 – 1.41 (m, 2H), 1.31 (s, 9H), 1.27 – 1.19 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.9, 150.4, 135.5, 127.5, 125.5, 45.5, 43.0, 34.5, 31.3, 29.7, 25.7
HRMS (ESI)	m/z calculated for [M+H]⁺: 274.2165, found: 274.2166

N-(4-methoxyphenyl)cyclohexanecarboxamide
Identifier	2f
¹H NMR (600 MHz, CDCl₃)	δ 7.44 – 7.38 (m, 3H), 6.85 – 6.79 (m, 2H), 3.76 (s, 3H), 2.20 (tt, J = 11.8, 3.5 Hz, 1H), 1.92 (dd, J = 13.6, 1.8 Hz, 2H), 1.84 – 1.78 (m, 2H), 1.71 – 1.65 (m, 2H), 1.52 (ddd, J = 24.7, 12.3, 3.2 Hz, 2H), 1.32 – 1.26 (m, 2H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.3, 156.2, 131.4, 121.7, 114.0, 55.4, 46.2, 29.6, 25.6
HRMS (ESI)	m/z calculated for [M+H]⁺: 234.1488, found: 234.1488

N-phenylcyclohexanecarboxamide
Identifier	2g
¹H NMR (600 MHz, CDCl₃)	δ 7.53 (app d, J = 7.8 Hz, 2H), 7.32 – 7.28 (m, 2H), 7.11 – 7.06 (m, 1H), 2.23 (tt, J = 11.7, 3.5 Hz, 1H), 1.95 (d, J = 13.4 Hz, 2H), 1.87 – 1.81 (m, 2H), 1.72 – 1.68 (m, 1H), 1.58 – 1.51 (m, 2H), 1.36 – 1.20 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.4, 138.1, 128.9, 124.0, 119.7, 46.5, 29.6, 25.7
HRMS (ESI)	m/z calculated for [M+H]⁺: 204.1382, found: 204.1383

N-(p-tolyl)cyclohexanecarboxamide
Identifier	2h
¹H NMR (600 MHz, CDCl₃)	δ 7.41 (d, J = 8.4 Hz, 2H), 7.31 (bs, 1H), 7.10 (d, J = 8.2 Hz, 2H), 2.30 (s, 3H), 2.21 (m, 1H), 1.94 (m, 2H), 1.85 – 1.80 (m, 2H), 1.72 – 1.67 (m, 1H), 1.53 (m, 2H), 1.33 – 1.23 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.3, 135.6, 133.6, 129.4, 119.8, 46.4, 29.6, 25.7, 20.8
HRMS (ESI)	m/z calculated for [M+H]⁺: 218.1539, found: 218.1540

N-(4-butylphenyl)cyclohexanecarboxamide
Identifier	2i
¹H NMR (600 MHz, CDCl₃)	δ 7.42 (d, J = 8.4 Hz, 2H), 7.21 (bs, 1H), 7.11 (d, J = 8.4 Hz, 2H), 2.59 – 2.53 (m, 2H), 2.21 (tt, J = 11.8, 3.5 Hz, 1H), 1.94 (m, 2H), 1.86 – 1.80 (m, 2H), 1.69 (m, 1H), 1.61 – 1.52 (m, 5H), 1.38 – 1.25 (m, 9H), 0.91 (t, J = 7.4 Hz, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.2, 138.8, 135.7, 128.8, 119.8, 46.5, 35.0, 33.7, 29.7, 25.7, 22.2, 13.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 260.2008, found: 260.2009

(3-((tert-butyldimethylsilyl)oxy)azetidin-1-yl)(cyclohexyl)methanone
Identifier	2j
¹H NMR (400 MHz, CDCl₃)	δ 4.62 – 4.54 (m, 1H), 4.28 (t, J = 7.7 Hz, 1H), 4.15 (dd, J = 10.1, 6.8 Hz, 1H), 3.94 (m, 1H), 3.78 (m, 1H), 2.11 (tt, J = 11.7, 3.5 Hz, 1H), 1.81 – 1.60 (m, 6H), 1.46 (m, 2H), 1.29 – 1.19 (m, 2H), 0.88 – 0.86 (m, 9H), 0.06 – 0.03 (m, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 176.3, 61.4, 60.2, 58.0, 40.4, 28.8, 28.7, 25.8, 25.8, 25.8, 18.0
HRMS (ESI)	m/z calculated for [M+H]⁺: 298.2196, found: 298.2197

cyclohexyl(morpholino)methanone
Identifier	2k
¹H NMR (500 MHz, CDCl₃)	δ 3.57 (dd, J = 43.8, 39.7 Hz, 8H), 2.41 (tt, J = 11.6, 3.4 Hz, 1H), 1.78 (m, 2H), 1.68 (t, J = 10.9 Hz, 3H), 1.51 (m, 2H), 1.31 – 1.19 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.7, 67.0, 66.8, 45.9, 41.9, 40.2, 29.3, 25.8, 25.8
HRMS (ESI)	m/z calculated for [M+H]⁺: 198.1488, found: 198.1489

cyclohexyl(piperidin-1-yl)methanone
Identifier	2l
¹H NMR (500 MHz, CDCl₃)	δ 3.56 – 3.33 (m, 4H), 2.44 (tt, J = 11.6, 3.4 Hz, 1H), 1.77 (dd, J = 8.7, 2.4 Hz, 2H), 1.72 – 1.59 (m, 5H), 1.55 – 1.43 (m, 6H), 1.31 – 1.18 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.5, 46.5, 42.8, 40.6, 29.6, 27.0, 26.0, 26.0, 25.8, 24.8
HRMS (ESI)	m/z calculated for [M+H]⁺: 196.1695, found: 196.1696

methyl (cyclohexanecarbonyl)valinate
Identifier	2m
¹H NMR (400 MHz, CDCl₃)	δ 5.93 (d, J = 8.5 Hz, 1H), 4.56 (dd, J = 8.9, 4.9 Hz, 1H), 3.72 (s, 3H), 2.14 (tdt, J = 8.0, 6.9, 4.1 Hz, 2H), 1.86 (m, 2H), 1.80 – 1.74 (m, 2H), 1.68 – 1.62 (m, 1H), 1.50 – 1.38 (m, 2H), 1.34 – 1.13 (m, 2H), 0.89 (dd, J = 13.5, 6.9 Hz, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 176.1, 173.0, 56.6, 52.2, 45.6, 31.5, 30.0, 29.5, 25.8, 25.7, 19.1, 17.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 242.1750, found: 242.1751

N-cycloheptylcyclohexanecarboxamide
Identifier	2n
¹H NMR (500 MHz, CDCl₃)	δ 5.39 (d, J = 5.2 Hz, 1H), 3.92 (qt, J = 8.7, 4.3 Hz, 1H), 1.99 (tt, J = 11.9, 3.4 Hz, 1H), 1.92 – 1.85 (m, 2H), 1.84 – 1.73 (m, 5H), 1.69 – 1.13 (m, 15H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.9, 50.1, 45.8, 35.3, 29.9, 28.1, 25.9, 24.3
HRMS (ESI)	m/z calculated for [M+H]⁺: 224.2008, found: 224.2009

N-(tert-butyl)cyclohexanecarboxamide
Identifier	2o
¹H NMR (500 MHz, CDCl₃)	δ 5.23 (s, 1H), 1.93 (tt, J = 11.8, 3.4 Hz, 1H), 1.78 (m, 5H), 1.64 (m, 2H), 1.43 – 1.35 (m, 3H), 1.32 (s, 9H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.7, 50.9, 46.5, 29.9, 29.0, 25.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 184.1695, found: 184.1695

tert-butyl 4-(cyclohexanecarbonyl)piperazine-1-carboxylate
Identifier	2p
¹H NMR (400 MHz, CDCl₃)	δ 3.60 – 3.25 (m, 8H), 2.42 (tt, J = 11.6, 3.3 Hz, 1H), 1.80 – 1.72 (m, 2H), 1.66 (dd, J = 7.9, 6.8 Hz, 3H), 1.55 – 1.46 (m, 2H), 1.43 (s, 9H), 1.30 – 1.14 (m, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 174.8, 154.6, 80.3, 45.3, 41.4, 40.5, 29.5, 28.4, 25.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 297.2172, found: 297.2173

N-cyclohexylcyclohexanecarboxamide
Identifier	2q
¹H NMR (600 MHz, CDCl₃)	δ 5.33 (bs, 1H), 3.79 – 3.72 (m, 1H), 2.02 (tt, J = 11.8, 3.5 Hz, 1H), 1.92 – 1.85 (m, 2H), 1.85 – 1.81 (m, 2H), 1.78 (m, 2H), 1.72 – 1.64 (m, 3H), 1.62 – 1.56 (m, 1H), 1.50 – 1.05 (m, 10H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.2, 47.8, 45.8, 33.4, 29.9, 25.9, 25.7, 25.0
HRMS (ESI)	m/z calculated for [M+H]⁺: 210.1852, found: 210.1853

N-(naphthalen-1-ylmethyl)cyclohexanecarboxamide
Identifier	2r
¹H NMR (600 MHz, CDCl₃)	δ 7.99 (dd, J = 8.2, 0.8 Hz, 1H), 7.87 (dd, J = 8.2, 1.2 Hz, 1H), 7.81 (p, J = 3.0 Hz, 1H), 7.56 – 7.49 (m, 2H), 7.42 (d, J = 5.3 Hz, 2H), 5.74 (bs, 1H), 4.87 (d, J = 5.3 Hz, 2H), 2.07 (tt, J = 11.8, 3.5 Hz, 1H), 1.84 (m, 2H), 1.76 (m, 3H), 1.66 – 1.61 (m, 1H), 1.51 – 1.42 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.6, 133.9, 133.8, 131.4, 128.7, 128.5, 126.7, 126.5, 126.0, 125.3, 123.6, 108.4, 45.6, 41.6, 29.6, 25.6
HRMS (ESI)	m/z calculated for [M+H]⁺: 268.1695, found: 268.1696

N-hexylcyclohexanecarboxamide
Identifier	2s
¹H NMR (600 MHz, CDCl₃)	δ 5.50 (bs, 1H), 3.21 (dt, J = 13.2, 6.7 Hz, 2H), 2.04 (tt, J = 11.8, 3.5 Hz, 1H), 1.83 (m, 2H), 1.79 – 1.72 (m, 2H), 1.68 – 1.62 (m, 1H), 1.50 – 1.36 (m, 4H), 1.30 (m, 3H), 1.26 – 1.17 (m, 5H), 0.89 – 0.84 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 176.2, 45.8, 39.4, 31.6, 29.9, 29.8, 26.6, 25.9, 22.76, 14.1
HRMS (ESI)	m/z calculated for [M+H]⁺: 212.2008 , found: 212.2009

N-(4-fluorophenyl)cyclohexanecarboxamide
Identifier	2t
¹H NMR (600 MHz, CDCl₃)	δ 7.50 – 7.44 (m, 2H), 7.23 (s, 1H), 7.02 – 6.95 (m, 2H), 2.21 (tt, J = 11.9, 3.6 Hz, 1H), 1.95 (m, 2H), 1.86 – 1.80 (m, 2H), 1.73 – 1.65 (m, 1H), 1.58 – 1.49 (m, 2H), 1.39 – 1.26 (m, 3H)
¹³C NMR (151 MHz, Chloroform-d)	δ 174.3, 159.2 (d, J = 243.1 Hz), 134.0 (d, J = 2.6 Hz), 121.5 (d, J = 7.8 Hz), 115.5 (d, J = 22.5 Hz), 46.4, 29.6, 25.6
¹⁹F NMR (565 MHz, CDCl₃)	δ -118.73 – -118.87 (m)
HRMS (ESI)	m/z calculated for [M+H]⁺: 222.1288, found: 222.1289

cyclohexyl(pyrrolidin-1-yl)methanone
Identifier	2u
¹H NMR (500 MHz, CDCl₃)	δ 3.50 – 3.33 (m, 4H), 2.32 (tt, J = 11.7, 3.4 Hz, 1H), 1.97 – 1.88 (m, 2H), 1.86 – 1.63 (m, 9H), 1.51 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.8, 46.3, 45.6, 42.9, 28.9, 26.2, 25.9, 25.8, 24.3
HRMS (ESI)	m/z calculated for [M+H]⁺: 182.1539, found: 182.1540

N-butylcyclohexanecarboxamide
Identifier	2v
¹H NMR (300 MHz, CDCl₃)	δ 5.40 (bs, 1H), 3.23 (td, J = 7.0, 5.7 Hz, 2H), 2.04 (tt, J = 11.7, 3.4 Hz, 1H), 1.91 – 1.60 (m, 7H), 1.50 – 1.29 (m, 7H), 0.92 (t, J = 7.2 Hz, 3H)
¹³C NMR (76 MHz, CDCl₃)	δ 176.1, 45.8, 39.2, 31.9, 29.9, 25.9, 20.2, 13.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 184.1695, found: 184.1696

N-(sec-butyl)cyclohexanecarboxamide
Identifier	2w
¹H NMR (600 MHz, CDCl₃)	δ 5.22 (bs, 1H), 3.94 – 3.84 (m, 1H), 2.02 (tt, J = 11.8, 3.5 Hz, 1H), 1.86 – 1.81 (m, 2H), 1.80 – 1.74 (m, 2H), 1.67 – 1.62 (m, 1H), 1.48 – 1.38 (m, 4H), 1.30 – 1.19 (m, 3H), 1.08 (d, J = 6.6 Hz, 3H), 0.88 (t, J = 7.5 Hz, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.4, 46.0, 45.7, 29.9, 29.7, 29.7, 25.8, 25.7, 25.7, 20.5, 10.3
HRMS (ESI)	m/z calculated for [M+H]⁺: 184.1695, found: 184.1696

N,N-diethylcyclohexanecarboxamide
Identifier	2x
¹H NMR (600 MHz, CDCl₃)	δ 3.35 (dd, J = 14.2, 7.1 Hz, 2H), 3.31 (dd, J = 14.3, 7.1 Hz, 2H), 2.43 – 2.36 (m, 1H), 1.82 – 1.77 (m, 3H), 1.71 – 1.66 (m, 4H), 1.61 – 1.51 (m, 3H), 1.18 (t, J = 7.1 Hz, 3H), 1.09 (t, J = 7.1 Hz, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.6, 41.8, 41.0, 40.2, 29.8, 26.1, 15.2, 13.3
HRMS (ESI)	m/z calculated for [M+H]⁺: 184.1695, found: 184.1696

N-(1-(2,6-dimethylphenoxy)propan-2-yl)cyclohexanecarboxamide
Identifier	2y
¹H NMR (600 MHz, CDCl₃)	δ 7.00 (dd, J = 7.5, 0.5 Hz, 2H), 6.92 (dd, J = 7.9, 7.0 Hz, 1H), 5.91 (bd, J = 7.8 Hz, 1H), 4.38 – 4.27 (m, 1H), 3.80 (dd, J = 9.1, 4.0 Hz, 1H), 3.70 (dd, J = 9.1, 3.0 Hz, 1H), 2.26 (s, 6H), 2.11 (tt, J = 11.8, 3.5 Hz, 1H), 1.93 – 1.87 (m, 2H), 1.83 – 1.77 (m, 2H), 1.71 – 1.66 (m, 1H), 1.49 – 1.42 (m, 2H), 1.40 (d, J = 6.9 Hz, 3H), 1.34 – 1.20 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.5, 155.0, 130.9, 129.1, 124.2, 74.1, 45.8, 45.1, 29.9, 29.8, 25.9, 25.9, 25.9, 18.0, 16.3
HRMS (ESI)	m/z calculated for [M+H]⁺: 290.2114, found: 290.2115

2,2-dimethyl-1-morpholinopropan-1-one
Identifier	2aa
¹H NMR (600 MHz, CDCl₃)	δ 3.68 – 3.62 (m, 8H), 1.28 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 176.7, 67.1, 45.9, 38.7, 28.5
HRMS (ESI)	m/z calculated for [M+H]⁺: 172.1332, found: 172.1332

N-cyclopentylnonanamide
Identifier	2ab
¹H NMR (400 MHz, CDCl₃)	δ 5.42 (bs, 1H), 4.25 – 4.13 (m, 1H), 2.12 (dd, J = 8.9, 6.4 Hz, 2H), 2.02 – 1.92 (m, 2H), 1.68 – 1.52 (m, 10H), 1.38 – 1.16 (m, 8H), 0.86 (t, J = 6.9 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 172.8, 51.0, 42.8, 37.0, 33.1, 31.8, 29.7, 29.3, 29.3, 29.1, 25.8, 23.7, 22.6, 14.1
HRMS (ESI)	m/z calculated for [M+H]⁺: 226.2165, found: 226.2166

N-cyclopentylpentanamide
Identifier	2ac
¹H NMR (400 MHz, CDCl₃)	δ 5.40 (bs, 1H), 4.26 – 4.15 (m, 1H), 2.17 – 2.09 (m, 2H), 2.04 – 1.92 (m, 2H), 1.71 – 1.55 (m, 6H), 1.40 – 1.29 (m, 4H), 0.91 (t, J = 7.3 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 172.9, 51.2, 36.9, 33.3, 28.1, 23.8, 22.5, 13.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 170.1539, found: 170.1540

3-cyclohexyl-1-(pyrrolidin-1-yl)propan-1-one
Identifier	2ad
¹H NMR (600 MHz, CDCl₃)	δ 3.45 (t, J = 6.9 Hz, 2H), 3.40 (t, J = 6.8 Hz, 2H), 2.28 – 2.20 (m, 2H), 1.94 (p, J = 6.8 Hz, 2H), 1.84 (p, J = 6.8 Hz, 2H), 1.73 – 1.61 (m, 7H), 1.53 (dd, J = 15.6, 7.2 Hz, 2H), 1.27 – 1.10 (m, 2H), 0.95 – 0.86 (m, 2H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.3, 46.7, 45.8, 37.6, 33.3, 32.5, 32.5, 26.7, 26.4, 26.38, 24.6
HRMS (ESI)	m/z calculated for [M+H]⁺: 210.1852, found: 210.1852

tert-butyl 4-(morpholine-4-carbonyl)piperidine-1-carboxylate
Identifier	2ae
¹H NMR (600 MHz, CDCl₃)	δ 4.11 (s, 2H), 3.64 (s, 4H), 3.53 (app d, J = 63.4 Hz, 4H), 2.73 (s, 2H), 2.56 (ddd, J = 11.0, 7.6, 4.0 Hz, 1H), 1.75 – 1.58 (m, 4H), 1.42 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 173.1, 154.7, 79.7, 67.0, 66.9, 46.0, 43.6, 42.9, 42.1, 38.3, 28.5, 28.4
HRMS (ESI)	m/z calculated for [M+H]⁺: 299.1965, found: 299.1966

4-(morpholine-4-carbonyl)cyclohexan-1-one
Identifier	2af
¹H NMR (500 MHz, CDCl₃)	δ 3.75 – 3.49 (m, 8H), 2.90 (dt, J = 14.2, 7.3 Hz, 1H), 2.55 (dt, J = 8.1, 3.7 Hz, 2H), 2.39 – 2.27 (m, 2H), 2.09 – 1.99 (m, 4H)
¹³C NMR (126 MHz, CDCl₃)	δ 210.0, 172.9, 67.1, 66.9, 46.3, 42.3, 40.0, 37.8, 28.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 212.1281, found 212.1283

cyclopentyl(morpholino)methanone
Identifier	2ag
¹H NMR (600 MHz, CDCl₃)	δ 3.66 – 3.62 (m, 4H), 3.61 (app d, J = 5.0 Hz, 2H), 3.53 – 3.44 (m, 2H), 2.84 (p, J = 8.0 Hz, 1H), 1.87 – 1.76 (m, 4H), 1.73 – 1.68 (m, 2H), 1.58 – 1.50 (m, 2H)
¹³C NMR (151 MHz, CDCl₃)	δ 174.7, 67.0, 66.7, 46.0, 42.1, 40.8, 30.0, 26.0
HRMS (ESI)	m/z calculated for [M+H]⁺: 184.1332, found: 184.1333

(6-(4-bromophenyl)tetrahydro-2H-pyran-3-yl)(pyrrolidin-1-yl)methanone
Identifier	2ah
Sample qualifier	The product was isolated as a mixture of diastereomers (d.r. 3:2)
¹H NMR (400 MHz, CDCl₃)	δ 7.47 – 7.41 (m, 3H), 7.28 – 7.18 (m, 3H), 5.05 (dd, J = 10.2, 2.8 Hz, 1H), 4.36 – 4.28 (m, 1H), 4.21 (ddd, J = 11.6, 4.6, 1.6 Hz, 1H), 4.12 – 4.02 (m, 1H), 3.93 – 3.87 (m, 1H), 3.63 (ddd, J = 12.7, 11.7, 2.2 Hz, 1H), 3.56 – 3.34 (m, 6H), 2.94 – 2.87 (m, 1H), 2.82 – 2.72 (m, 1H), 2.08 – 1.75 (m, 12H), 1.71 – 1.63 (m, 1H)
¹³C NMR (126 MHz, CDCl₃)	δ 173.9, 172.5, 142.2, 141.5, 131.5, 131.5, 127.9, 127.9, 121.5, 121.1, 78.7, 74.6, 67.9, 64.4, 46.6, 46.5, 46.0, 46.0, 40.7, 35.8, 35.0, 34.3, 28.1, 27.1, 26.4, 26.3, 24.3, 24.3
HRMS (ESI)	m/z calculated for [M+H]⁺: 338.0750, found: 338.0751

cycloheptyl(morpholino)methanone
Identifier	2ai
¹H NMR (600 MHz, CDCl₃)	δ 5.30 (bs, 1H), 4.21 – 4.14 (m, 1H), 2.17 – 2.11 (m, 1H), 2.01 – 1.94 (m, 2H), 1.88 – 1.82 (m, 2H), 1.78 – 1.72 (m, 3H), 1.67 – 1.54 (m, 8H), 1.48 – 1.40 (m, 3H), 1.37 – 1.29 (m, 2H)
¹³C NMR (151 MHz, CDCl₃)	δ 176.8, 50.9, 47.6, 33.2, 31.7, 28.1, 26.7, 23.8
HRMS (ESI)	m/z calculated for [M+H]⁺: 210.1852, found: 210.1853

(1S,4R)-N-cyclopentylbicyclo[2.2.1]heptane-2-carboxamide
Identifier	2aj
¹H NMR (600 MHz, CDCl₃)	δ 5.37 (bs, 1H), 4.23 – 4.06 (m, 1H), 2.35 – 2.29 (m, 1H), 2.27 (s, 1H), 2.05 – 2.01 (m, 1H), 1.99 – 1.91 (m, 2H), 1.83 (dddd, J = 9.5, 5.1, 4.4, 2.7 Hz, 1H), 1.68 – 1.61 (m, 2H), 1.61 – 1.55 (m, 3H), 1.54 – 1.46 (m, 2H), 1.43 – 1.38 (m, 1H), 1.36 – 1.28 (m, 2H), 1.20 – 1.10 (m, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 175.4, 51.2, 48.3, 41.7, 36.6, 36.1, 34.5, 33.4, 33.3, 30.0, 28.8, 23.9, 23.9
HRMS (ESI)	m/z calculated for [M+H]⁺: 208.1695, found: 208.1696

(1-(pyrimidin-2-yl)piperidin-4-yl)(pyrrolidin-1-yl)methanone
Identifier	2ak
¹H NMR (600 MHz, CDCl₃)	δ 8.29 (d, J = 4.7 Hz, 2H), 6.45 (t, J = 4.7 Hz, 1H), 4.83 – 4.76 (m, 2H), 3.52 (t, J = 6.8 Hz, 2H), 3.47 (t, J = 7.0 Hz, 2H), 2.93 (ddd, J = 13.4, 11.4, 4.0 Hz, 2H), 2.63 (ddd, J = 15.2, 10.0, 4.8 Hz, 1H), 1.98 (p, J = 6.8 Hz, 2H), 1.89 – 1.84 (m, 2H), 1.84 – 1.76 (m, 4H)
¹³C NMR (151 MHz, CDCl₃)	δ 173.2, 161.6, 157.7, 109.6, 46.4, 45.8, 43.4, 41.2, 27.8, 26.2, 24.3
HRMS (ESI)	m/z calculated for [M+H]⁺: 261.1709, found: 261.1710

(4-(tert-butyl)cyclohexyl)(pyrrolidin-1-yl)methanone
Identifier	2al
¹H NMR (500 MHz, CDCl₃)	δ 3.45 (q, J = 7.0 Hz, 4H), 2.25 (ddd, J = 18.3, 10.9, 4.9 Hz, 1H), 1.93 (dd, J = 13.5, 6.8 Hz, 2H), 1.87 – 1.77 (m, 2H), 1.54 (dd, J = 24.1, 11.8 Hz, 4H), 1.10 – 0.96 (m, 5H), 0.84 (s, 9H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.0, 47.4, 46.5, 45.8, 43.2, 32.6, 29.4, 27.6, 26.9, 26.3, 24.5
HRMS (ESI)	m/z calculated for [M+H]⁺: 238.2165, found: 238.2166

pyrrolidin-1-yl(1,4-dioxaspiro[4.5]decan-8-yl)methanone
Identifier	2am
¹H NMR (500 MHz, CDCl₃)	δ 3.96 – 3.89 (m, 4H), 3.45 (dt, J = 9.6, 6.9 Hz, 4H), 2.34 (tt, J = 11.4, 3.4 Hz, 1H), 1.97 – 1.91 (m, 2H), 1.90 – 1.80 (m, 6H), 1.78 – 1.71 (m, 2H), 1.52 (td, J = 13.2, 3.9 Hz, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 174.0, 108.2, 64.4, 64.4, 46.5, 45.9, 41.6, 34.3, 26.5, 26.3, 24.4
HRMS (ESI)	m/z calculated for [M+H]⁺: 240.1594, found: 240.1594

(2,3-dihydro-1H-inden-2-yl)(pyrrolidin-1-yl)methanone
Identifier	2an
¹H NMR (500 MHz, CDCl₃)	δ 7.21 – 7.17 (m, 2H), 7.17 – 7.11 (m, 2H), 3.57 – 3.49 (m, 4H), 3.43 (p, J = 8.6 Hz, 1H), 3.32 (dd, J = 15.4, 8.9 Hz, 2H), 3.12 (dd, J = 15.2, 8.5 Hz, 2H), 1.99 (p, J = 6.9 Hz, 2H), 1.89 (p, J = 6.9 Hz, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 173.3, 142.1, 126.6, 124.3, 46.7, 46.1, 43.8, 36.4, 26.3, 24.5
HRMS (ESI)	m/z calculated for [M+H]⁺: 216.1382, found: 216.1383

3-(6-methoxynaphthalen-2-yl)-1-(pyrrolidin-1-yl)butan-1-one
Identifier	2ao
¹H NMR (500 MHz, CDCl₃)	δ 7.68 (dd, J = 8.5, 4.3 Hz, 2H), 7.60 (s, 1H), 7.37 (dd, J = 8.5, 1.4 Hz, 1H), 7.15 – 7.08 (m, 2H), 3.91 (s, 3H), 3.53 (dq, J = 13.7, 7.0 Hz, 1H), 3.47 – 3.30 (m, 3H), 3.12 (dt, J = 13.4, 6.8 Hz, 1H), 2.58 (ddd, J = 22.5, 14.7, 7.0 Hz, 2H), 1.88 – 1.69 (m, 3H), 1.42 (d, J = 6.9 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 170.6, 157.4, 141.8, 133.4, 129.2, 129.2, 127.0, 126.4, 124.9, 118.8, 105.7, 55.4, 46.8, 45.7, 43.8, 36.5, 26.1, 24.5, 21.6
HRMS (ESI)	m/z calculated for [M+H]⁺: 298.1801, found: 298.1802

1,3-dimethyl-7-(2-methyl-3-oxo-3-(pyrrolidin-1-yl)propyl)-3,7-dihydro-1H-purine-2,6-dione
Identifier	2ap
Sample qualifier	The product contains an impurity which is identified as the photocatalyst [Ir(dtbbpy)(ppy)₂]PF₆
¹H NMR (600 MHz, CDCl₃)	δ 7.64 (s, 1H), 3.59 (s, 2H), 3.42 (s, 3H), 3.41 – 3.37 (m, 2H), 3.37 – 3.33 (m, 2H), 3.30 – 3.27 (m, 1H), 1.94 – 1.86 (m, 2H), 1.84 – 1.78 (m, 2H), 1.19 (d, J = 7.0 Hz, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 171.6, 155.2, 151.7, 149.1, 142.7, 106.6, 49.6, 46.4, 45.9, 39.4, 30.6, 28.0, 26.0, 24.3, 24.2, 14.9, 13.7
HRMS (ESI)	m/z calculated for [M+H]⁺: 320.1717, found: 320.1718

((3r,5r,7r)-adamantan-1-yl)(piperidin-1-yl)methanone
Identifier	2aq
¹H NMR (400 MHz, CDCl₃)	δ 3.64 – 3.53 (m, 4H), 2.02 (app dd, J = 15.3, 4.1 Hz, 9H), 1.72 (s, 6H), 1.67 – 1.61 (m, 2H), 1.55 (s, 4H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.6, 46.5, 41.7, 39.1, 36.7, 28.6, 26.4, 24.8
HRMS (ESI)	m/z calculated for [M+H]⁺: 248.2008, found: 248.2009

o-tolyl cyclohexanecarboxylate
Identifier	3b
¹H NMR (500 MHz, Chloroform-d)	δ 7.24 – 7.16 (m, 2H), 7.12 (td, J = 7.4, 1.4 Hz, 1H), 7.01 – 6.94 (m, 1H), 2.59 (tdt, J = 11.1, 7.3, 3.7 Hz, 1H), 2.17 (s, J = 0.7 Hz, 3H), 2.14 – 2.05 (m, 2H), 1.83 (m, 2H), 1.75 – 1.67 (m, 1H), 1.67 – 1.57 (m, 2H), 1.43 – 1.28 (m, 3H)
¹³C NMR (126 MHz, Chloroform-d)	δ 174.3, 149.4 (d, J = 3.7 Hz), 133.7 (d, J = 19.4 Hz), 131.1, 130.1 (d, J = 1.3 Hz), 128.7, 128.5 (d, J = 6.9 Hz), 126.9, 125.8, 121.9 (d, J = 1.2 Hz), 43.3 (d, J = 58.1 Hz), 29.1 (d, J = 1.6 Hz), 25.7, 25.4 (d, J = 4.3 Hz), 16.2
HRMS (ESI)	m/z [M+Na]⁺ calculated for [Na]⁺: 242.1233, found: 242.1233

4-chlorophenyl cyclohexanecarboxylate
Identifier	3c
¹H NMR (500 MHz, Chloroform-d)	δ 7.36 – 7.29 (m, 2H), 7.04 – 6.97 (m, 2H), 2.54 (tdt, J = 11.1, 7.3, 3.7 Hz, 1H), 2.10 – 1.99 (m, 2H), 1.82 (m, 2H), 1.75 – 1.65 (m, 1H), 1.65 – 1.49 (m, 2H), 1.34 (m, 3H)
¹³C NMR (126 MHz, Chloroform-d)	δ 174.3, 149.4 (d, J = 3.8 Hz), 131.0, 129.4, 122.9 (d, J = 1.4 Hz), 43.1 (d, J = 58.3 Hz), 28.9 (d, J = 1.6 Hz), 25.7, 25.3 (d, J = 4.3 Hz)
HRMS (ESI)	m/z [M+Na]⁺ calculated for [Na]⁺: 262.0687, found: 262.0687

3-methoxyphenyl cyclohexanecarboxylate
Identifier	3d
¹H NMR (500 MHz, Chloroform-d)	δ 7.26 (d, J = 16.4 Hz, 1H), 6.77 (ddd, J = 8.4, 2.6, 0.9 Hz, 1H), 6.66 (ddt, J = 8.1, 2.3, 0.8 Hz, 1H), 6.62 (t, J = 2.3 Hz, 1H), 3.79 (s, 3H), 2.55 (tdt, J = 11.2, 7.4, 3.7 Hz, 1H), 2.13 – 1.99 (m, 2H), 1.90 – 1.78 (m, 2H), 1.74 – 1.65 (m, 1H), 1.65 – 1.53 (m, 2H), 1.34 (m, 3H)
¹³C NMR (126 MHz, Chloroform-d)	δ 174.4, 160.5, 151.9 (d, J = 3.8 Hz), 129.7, 113.8 (d, J = 1.4 Hz), 111.5, 107.6 (d, J = 1.4 Hz), 43.2 (d, J = 58.3 Hz), 29.0 (d, J = 1.6 Hz), 25.7, 25.4 (d, J = 4.3 Hz)
HRMS (ESI)	m/z [M+Na]⁺ calculated for [Na]⁺: 258.1182, found: 258.1182