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1 Supporting Information B(C 6 F 5 ) 3 -catalyzed Regioselective Deuteration of Electronrich Aromatic and Heteroaromatic compounds Wu Li, Ming-Ming Wang, Yuya Hu and Thomas Werner* Leibniz-Institute of Catalysis e.v. at the University of Rostock, Albert-Einstein-Strasse 29a, Rostock, Germany. Content 1. General Considerations S2 2. General Procedures (GP) for the deuterium incorporation into aromatic and hetero-aromatic compounds using D 2 O as deuterium source S2 3 Additional experimental results S3 4. Characterization of the synthesized deuterated products S3 5. General Procedures (GP) for the dedeuteration of aromatic and heteroaromatic compounds S13 6. Characterization of the synthesized dedeuterated products S H NMR and 13 C NMR S15 8. References S63 S1

2 1. General Considerations All chemicals were purchased from commercial sources with purities 95% and used without further purification. Tris(pentafluorophenyl)borane was purchased from TCI in a purity >98.0% (NMR) and used without further purification. D 2 O (99.9% D) was purchased and deuterated solvents were ordered from Deutero GmbH and stored over molecular sieves. NMR spectra were received using Bruker 300 Fourier, Bruker AV 300 and Bruker AV 400 spectrometers. Chemical shifts are reported in ppm relative to the deuterated solvent. Coupling constants are expressed in Hertz (Hz). The following abbreviations are used: s= singlet, d= doublet, t= triplet and m= multiplet. High resolution mass spectra (HRMS) were obtained either from a MAT 95 XP from Thermo (EI) or from an HPLC system 1200 and downstream ESI-TOF-MS 6210 from Agilent (ESI). Thin layer chromatography was performed on Merck TLCplates with fluorescence indication (silica type 60, F 254 ), spots were visualized using UV-light or vanilline. Column chromatography was performed using silica with a grain size of µm from Macherey-Nagel. If not otherwise stated cyclohexane (CH) and ethyl acetate EtOAc were used as mobile phase. 2. General Procedures (GP) for the deuterium incorporation into aromatic and hetero-aromatic compounds using D 2 O as deuterium source A 25 cm 3 pressure tube equipped with screw cap and stir bar was charged with B(C 6 F 5 ) 3 (0.05 equiv) aromatic or hetero-aromatic compound 1 (0.5 mmol, 1.0 equiv) and D 2 O (30 equiv). The reaction mixture was heated to 80 C. After 24 h the mixture was cooled to room temperature and directly purified by flash chromatography simple filtration though a small pad of SiO 2 (CH:EtOAc= 20:1). After removal of all volatiles in vacuum the product 2 was obtained. S2

3 3. Additional experimental results entry variation from standard conditions deuterium incorporation (%) b D2O (3 equiv) 64 3 D2O (10 equiv) 85 4 D2O (20 equiv) o C instead of 80 o C 87 a Standard reaction conditions: 1a (0.5 mmol), B(C6F5)3 (0.025 mmol), D2O (15 mmol), CDCl3 (1.0 ml), 80 o C for 24 h. b Deuterium incorporation was determined by 1 H NMR. 4. Characterization of the synthesized deuterated products N,N-Dibenzylaniline-2,4,6-d 3 (2a) According to the GP, N,N-dibenzylaniline (1a,140 mg, mmol), B(C 6 F 5 ) 3 (17.0 mg, mmol) and D 2 O (306 mg, 15.3 mmol) were converted. After workup the product 2a (134 mg, mmol, 95%) was obtained as a light yellow solid (m.p o C). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 12H), (m, 0.12H), 4.61 (s, 4H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , , , , HRMS (ESI- TOF/MS): m/z calcd. C 10 H 12 D 3 N [M + +H]: ; m/z found C 10 H 12 D 3 N [M + +H]: N,N-Diethylaniline-2,4,6-d 3 (2b) 1 S3

4 According to the GP, N,N-diethylaniline (1b, 90 mg, 0.60 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (376 mg, 18.8 mmol) were converted. After workup the product 2b (88 mg, mmol, 96%) was obtained after chromatography as a colorless oil. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (d, J = 8.8 Hz, 0.82H), (m, 0.05H), (q, J = 7.0 Hz, 4H), (t, J = 7.1 Hz, 6H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , 44.39, HRMS (ESI-TOF/MS): m/z calcd. C 10 H 12 D 3 N [M + +H]: ; m/z found C 10 H 12 D 3 N [M + +H]: (Methyl(phenyl-2,4,6-d 3 )amino)propanenitrile-2,4,6-d 3 (2c) According to the GP, 3-(methyl(phenyl)amino)propanenitrile (1c, 83 mg, 0.52 mmol), B(C 6 F 5 ) 3 (16 mg, mmol) and D 2 O (214 mg, 10.7 mmol) were converted to the desired product. After workup the product 2c (85 mg, 0.52 mmol, >99%) was obtained as a light yellow liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 7.31 (d, J = 3.7 Hz, 2H), (t, J = 7.3 Hz, 0.10H), (m, 0.17H), (dd, J = 7.8, 6.0 Hz, 2H), 3.04 (s, 3H), (m, 2H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , , , 48.88, 38.56, HRMS (ESI-TOF/MS): m/z calcd. C 10 H 9 D 3 N 2 [M + +H]: ; m/z found C 10 H 9 D 3 N 2 [M + +H]: (Phenyl-2,3,4,5,6-d 5 )pyrrolidine (2d) 1 According to the GP, 1-phenylpyrrolidine (1d, 76 mg, 0.52 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (191 mg, 9.50 mmol) were converted to the desired product. After workup the product 2d (78 mg, mmol, 99%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 7.29 (s, 1H), (t, J = 7.3 Hz, 0.08H), (d, J = 8.6 Hz, 0.12H), (ddd, J = 6.6, 4.2, 2.6 Hz, 4H), S4

5 (m, 4H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , 47.65, HRMS (ESI-TOF/MS): m/z calcd. C 10 H 10 D 3 N [M + +H]: ; m/z found C 10 H 10 D 3 N [M + +H]: (Phenyl-2,4,6-d 3 )piperidine (2e) According to the GP, 1-phenylpiperidine (1e, 81 mg, 0.50 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (316 mg, 15.8 mmol) were converted to the desired product. After workup the product 2e (83 mg, 0.50 mmol, >99%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (dd, J = 9.4, 2.7 Hz, 1.45H), (t, J = 7.2 Hz, 0.43H), (m, 4H), (m, 4H), (m, 2H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , 50.75, 25.96, HRMS (ESI-TOF/MS): m/z calcd. C 11 H 12 D 3 N [M + +H]: ; m/z found C 11 H 12 D 2 N [M + +H]: (Phenyl-2,4,6-d 3 )morpholine-2,4,6-d 3 (2f) According to the GP, 4-phenylmorpholine (1f, 84 mg, 0.51 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (327 mg, 16.3 mmol) were converted to the desired product. After workup the product 2f (85 mg, mmol, >99%) was obtained as a white solid (m.p o C). 1 H NMR (300 MHz, CDCl 3 ) δ 7.34 (d, J = 3.9 Hz, 2H), (d, J= 8.7 Hz, 0.47H), (m, 4H), (m, 4H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , , 66.94, HRMS (ESI-TOF/MS): m/z calcd. C 10 H 10 D 3 NO [M + +H]: ; m/z found C 10 H 10 D 3 NO [M + +H]: S5

6 N,N,3-Trimethylaniline-2,4,6-d 3 (2g) According to the GP, N,N,3-trimethylaniline (1g, 81 mg, 0.60 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (340 mg, 17.0 mmol) were converted to the desired product. After workup the product 2g (72 mg, 0.52 mmol, 87%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 7.27 (d, J = 1.6 Hz, 1H), (d, J = 3.2 Hz, 0.15H), 3.04 (s, 6H), 2.45 (s, 3H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , 40.77, 27.03, HRMS (ESI-TOF/MS): m/z calcd. C 9 H 10 D 3 N [M + +H]: ; m/z found C 9 H 10 D 3 N [M + +H]: N,N,4-Trimethylaniline-2,6-d 2 (2h) 1 According to the GP, N,N,4-trimethylaniline (1h, 70 mg, 0.52 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (330 mg, 16.5 mmol) were converted to the desired product. After workup the product 2h (60 mg, 0.44 mmol, 84%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 7.12 (s, 2H), (d, J = 9.0 Hz, 0.20H), 2.94 (s, 6H), 2.31 (s, 3H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , 41.16, HRMS (ESI-TOF/MS): m/z calcd. C 9 H 11 D 2 N [M + +H]: ; m/z found C 9 H 11 D 2 N [M + +H]: N,N,3,5-Tetramethylaniline-2,4,6-d 3 (2i) 1 According to the GP, N,N,3,5-tetramethylaniline (1i, 77 mg, 0.52 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (210 mg, 10.5 mmol) were converted to the desired product. After workup the product 2i (75 mg, 0.49 mmol, 94%) was obtained as a light yellow liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 6.30 (s, 0.19H), 2.82 (s, 6H), 2.20 (s, S6

7 6H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , 41.16, HRMS (ESI-TOF/MS): m/z calcd. C 10 H 12 D 3 N [M + +H]: ; m/z found C 10 H 12 D 3 N [M + +H]: Methoxy-N,N-dimethylaniline-2,4,6-d 3 (2j) 1 According to the GP, 3-methoxy-N,N-dimethylaniline (1j, 80 mg, 0.53 mmol), B(C 6 F 5 ) 3 (14 mg, mmol) and D 2 O (320 mg, 16.0 mmol) were converted to the desired product. After workup the product 2j (78 mg, 0.51 mmol, 96%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 7.22 (s, 1H), (dd, J = 19.4, 8.3 Hz, 0.22H), 3.83 (s, 3H), 2.97 (s, 6H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , , , 99.18, 98.55, 55.10, HRMS (ESI-TOF/MS): m/z calcd. C 9 H 10 D 3 NO [M + +H]: ; m/z found C 9 H 10 D 3 NO [M + +H] Chloro-N,N-dimethylaniline-2,4,6-d 3 (2k) 1 According to the GP, 3-chloro-N,N-dimethylaniline (1k, 79 mg, 0.51 mmol), B(C 6 F 5 ) 3 (17 mg, mmol) and D 2 O (298 mg, 14.9 mmol) were converted to the desired product. After workup the product 2k (75 mg, 0.47 mmol, 93%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 7.21 (s, 1H), (m, 0.08H), (m, 0.04H), 2.96 (s, 6H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , 40.56, 40.42, HRMS (ESI- TOF/MS): m/z calcd. C 8 H 7 D 3 ClN [M + +H]: ; m/z found C 8 H 7 D 3 ClN [M + +H]: S7

8 4-Bromo-N,N,3-trimethylaniline-2,6-d 2 (2l) According to the GP, 4-bromo-N,N,3-trimethylaniline (1l, 106 mg, mmol), B(C 6 F 5 ) 3 (15 mg, mmol) and D 2 O (204 mg, 10.2 mmol) were converted to the desired product. After workup the product 2l (108 mg, mmol, >99%) was obtained as a white solid (m.p o C). 1 H NMR (300 MHz, CDCl 3 ) δ 7.35 (d, J = 1.1 Hz, 1H), 6.61 (s, 0.05H), (d, J = 8.8 Hz, 0.05H), 2.92 (s, 6H), 2.37 (s, 3H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , 40.88, 21.82, HRMS (ESI-TOF/MS): m/z calcd. C 9 H 10 D 2 BrN [M + +H]: ; m/z found C 9 H 10 D 2 BrN [M + +H]: Tris(phenyl-2,4,6-d3)amine (2m) According to the GP, triphenylamine (1m, 125 mg, mmol), B(C 6 F 5 ) 3 (12 mg, mmol) and D 2 O (757 mg, 37.9 mmol) were converted to the desired product. After workup the product 2m (128 mg, mmol, 98%) was obtained as a white solid (m.p o C). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 6H), 7.19 (d, J = 8.5 Hz, 2H), 7.16 (m, 0.19H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , , , , HRMS (ESI-TOF/MS): m/z calcd. C 18 H 6 D 9 N [M + +H]: ; m/z found C 18 H 6 D 9 N [M + +H]: S8

9 N,N-Dimethylnaphthalen-1-amine-2,3,4,6,7-d 5 (2n) 1 According to the GP, N,N-dimethylnaphthalen-1-amine (1n, 96 mg, 0.56 mmol), B(C 6 F 5 ) 3 (14 mg, mmol) and D 2 O (214 mg, 10.7 mmol) were converted to the desired product. After workup the product 2n (95 mg, 0.55 mmol, 98%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 1H), (m, 2.1H), 7.48 (s, 0.7H), (d, J = 7.5 Hz, 0.05H), 2.99 (s, 6H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , HRMS (ESI-TOF/MS): m/z calcd. C 12 H 8 D 5 N [M + +H]: ; m/z found C 12 H 8 D 5 N [M + +H]: ,3,6,7-Betrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-d (2o) According to the GP, 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline (1o, 87 mg, 0.50 mmol), B(C 6 F 5 ) 3 (13 mg, mmol) and D 2 O (217 mg, 10.9 mmol) were converted to the desired product. After workup the product 2o (74 mg, 0.43 mmol, 85%) was obtained as a light yellow liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (t, J = 7.4 Hz, 0.35H), (m, 4H), (t, J = 6.6 Hz, 4H), (m, 4H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , 50.14, 27.75, 27.02, HRMS (ESI-TOF/MS): m/z calcd. C 12 H 14 DN [M + +H]: ; m/z found C 12 H 14 DN [M + +H]: Methyl-1H-indole-2,3,5,7-d 4 (2p) (86%) D (82%) D D (44%) D N (86%) Me S9

10 According to the GP, 1-methyl-1H-indole (1p, 66 mg, 0.50 mmol), B(C 6 F 5 ) 3 (14 mg, mmol) and D 2 O (312 mg, 15.6 mmol) were converted to the desired product. After workup the product 2p (68 mg, 0.50 mmol, >99%) was obtained as a light yellow liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 0.18H), 7.31 (s, 1H), (m, 0.28H), 6.58 (s, 0.56H), 3.87 (s, 3H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , HRMS (ESI-TOF/MS): m/z calcd. C 9 H 5 D 4 N [M + +H]: ; m/z found C 9 H 5 D 4 N [M + +H]: ,2,3,4-Tetrahydroquinoline-6,8-d 2 (2q) According to the GP, 1,2,3,4-tetrahydroquinoline (1q, 77 mg, 0.57 mmol), B(C 6 F 5 ) 3 (12 mg, mmol) and D 2 O (309 mg, 15.5 mmol) were converted to the desired product. After workup the product 2q (75 mg, 0.55 mmol, 97%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (ddd, J = 4.8, 2.3, 1.2 Hz, 2H), (t, J = 7.4 Hz, 0.05H), (m, 0.07H), 3.84 (s, 1H), (m, 2H), (t, J = 6.4 Hz, 2H), (m, 2H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , , , , 55.34, 42.04, 27.04, HRMS (ESI-TOF/MS): m/z calcd. C 9 H 9 D 2 N [M + +H]: ; m/z found C 9 H 9 D 2 N [M + +H]: Hexadecylthiophene-2,4,5-d 3 (2r) According to the GP, 3-hexadecylthiophene (1r, 160 mg, mmol), B(C 6 F 5 ) 3 (12 mg, mmol) and D 2 O (308 mg, 15.4 mmol) were converted to the desired product. After workup the product 2r (156 mg, mmol, 97%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (d, J = 4.9 Hz, 0.80H), (d, J = 4.9 Hz, 1H), (m, 2H), (m, 2H), (m, 26H), (m, 3H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , 32.10, 30.72, 30.41, 29.87, 29.83, 29.77, 29.64, 29.54, 29.51, 22.87, S10

11 1-Benzyl-1H-pyrrole-2,3,4,5-d 4 (2s) 2 According to the GP, 1-benzyl-1H-pyrrole (1s, 103 mg, mmol), B(C 6 F 5 ) 3 (12 mg, mmol) and D 2 O (327 mg, 16.0 mmol) were converted to the desired product. After workup the product 2s (96 mg, 0.60 mmol, 91%) was obtained as a light yellow liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 3H), (m, 2H), 6.74 (t, J = 1.1 Hz, 1.05H), (d, J = 1.9 Hz, 0.47H), 5.11 (s, 2H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , 53.42, ,3-Dimethoxybenzene-2,4,5,6-d 4 (2t) 3 According to the GP, 1,3-dimethoxybenzene (1t, 75 mg, 0.54 mmol), B(C 6 F 5 ) 3 (12 mg, mmol) and D 2 O (321 mg, 16.0 mmol) were converted to the desired product. After workup the product 2t (73 mg, 0.52 mmol, 96%) was obtained as a colorless liquid. 1 H NMR (300 MHz, CDCl 3 ) δ 7.25 (s, 0.91H), (m, 0.16H), 6.54 (s, 0.63H), 3.85 (d, J = 0.5 Hz, 6H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , , , , , , ,3,5-Trimethoxybenzene-2,4,6-d 3 (2u) 4 According to the GP, 1,3,5-trimethoxybenzene (1u, 84 mg, 0.50 mmol), B(C 6 F 5 ) 3 (14 mg, mmol) and D 2 O (300 mg, 15.0 mmol) were converted to the desired product. After workup the product 2u (86 mg, 0.50 mmol, >99%) was obtained (hexane:ethyl acetate = 10:1) as a white solid. 1 H NMR (400 MHz, CDCl 3 ) δ 6.08 (s, 0.26H), 3.76 (s, 9H). 13 C{ 1 H} NMR (100 MHz, cdcl 3 ) δ , 92.92, 92.66, 92.42, S11

12 HRMS (ESI-TOF/MS): m/z calcd. C 9 H 9 D 3 O 3 [M + +H]: ; m/z found C 9 H 9 D 3 O 3 [M + +H]: ,4,6-Trimethoxybenzaldehyde-3,5-d 2 (2v) According to the GP, 2,4,6-trimethoxybenzaldehyde (1v, 100 mg, mmol), B(C 6 F 5 ) 3 (12 mg, mmol) and D 2 O (306 mg, 15.0 mmol) were converted to the desired product. After workup the product 2v (99 mg, 0.50 mmol, 98%) was obtained (pure ethyl acetate) as a white solid. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 0.93H), 6.01 (s, 1.04H), 3.81 (t, J = 1.1 Hz, 9H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ , , , , 90.22, 90.19, 55.95, HRMS (ESI-TOF/MS): m/z calcd. C 10 H 10 D 2 O 4 [M + +H]: ; m/z found C 10 H 10 D 2 O 4 [M + +H]: N-(2-(5-Methoxy-1H-indol-3-yl-2,4,6-d 3 )ethyl)acetamide (4) According to the GP, N-(2-(5-methoxy-1H-indol-3-yl-2,4,6-d3)ethyl)acetamide (118 mg, mmol), B(C 6 F 5 ) 3 (14 mg, mmol) and D 2 O (306 mg, 15.3 mmol) were converted to the desired product. After workup the product 4 (114 mg, mmol, 95%) was obtained as a white solid (m.p o C). 1 H NMR (300 MHz, DMSO-d 6 ) δ 7.22 (s, 1H), 7.10 (t, J = 0.8 Hz, 0.09H), (m, 0.09H), (d, J = 8.7 Hz, 0.17H), 3.76 (s, 3H), (m, 2H), (m, 2H), 1.81 (s, 3H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) , , , , , , , , , , , , , 55.49, 40.52, 40.24, 39.96, 39.82, 39.68, 39.41, 39.13, 38.85, 25.46, 22.90, HRMS (ESI-TOF/MS): m/z calcd. C 13 H 13 D 3 N 2 O 2 [M + +H]: ; m/z found C 13 H 13 D 3 N 2 O 2 [M + +H]: S12

13 5. General Procedures (GP) for the dedeuteration of aromatic and hetroaromatic compounds: A 25 cm 3 pressure tube equipped with screw cap and stir bar was charged with B(C 6 F 5 ) 3 (0.05 equiv) aromatic or hetro-aromatic deuterated compound 2 (0.5 mmol, 1.0 equiv) and H 2 O (30 equiv). The reaction mixture was heated to 80 C. After 24 h the mixture was cooled to room temperature and directly purified by flash chromatography simple filtration though a small pad of SiO 2 (CH:EtOAc= 20:1). After removal of all volatiles in vacuum the product 1 was obtained. 6. Characterization of the synthesized dedeuterated products N,N-Dibenzylaniline-2,4,6 (1a) According to the GP, N,N-dibenzylaniline-d 3 (2a,133 mg, mmol), B(C 6 F 5 ) 3 (13.0 mg, mmol) and H 2 O (254 mg, 14.1 mmol) were converted. After workup the product 1a (130 mg, mmol, 96%) was obtained as a white solid. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 12H), (m, 3H), 4.72 (s, 4H). 1-Methyl-1H-indole (1p) According to the GP, 1-methyl-1H-indole-2,3,5,7-d 4 (2p, 68 mg, 0.50 mmol), B(C 6 F 5 ) 3 (14 mg, mmol) and H 2 O (270 mg, 15.0 mmol) were converted to the desired product. After workup the product 1p (66 mg, 0.50 mmol, >99%) was obtained as a light yellow liquid. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 1H), (m, 1H), (m, 1H), 7.06 (d, J = 3.1 Hz, 1H), 6.50 (dd, J = 3.1, 0.8 Hz, 1H), 3.81 (s, 3H). S13

14 1,3,5-Trimethoxybenzene (1u) According to the GP, 1,3,5-trimethoxybenzene-2,4,6-d 3 (2u, 86 mg, 0.50 mmol), B(C 6 F 5 ) 3 (14 mg, mmol) and H 2 O (270 mg, 15.0 mmol) were converted to the desired product. After workup the product 1u (83 mg, 0.49 mmol, 98%) was obtained (hexane:ethyl acetate = 10:1) as a white solid. 1 H NMR (400 MHz, CDCl 3 ) δ 6.09 (s, 3H), 3.77 (s, 9H). S14

15 7. 1 H and 13 C NMR spectra 1 H NMR spectrum of substrate 1a: 1 H NMR spectrum of product 2a: S15

16 13 C NMR spectrum of product 2a: S16

17 1 H NMR spectrum of substrate 1b: 1 H NMR spectrum of product 2b: S17

18 13 C NMR spectrum of product 2b: S18

19 1 H NMR spectrum of substrate 1c: Me N CN 1 H NMR spectrum of product 2c: S19

20 13 C NMR spectrum of product 2c: S20

21 1 H NMR spectrum of substrate 1d: 1 H NMR spectrum of product 2d: S21

22 13 C NMR spectrum of product 2d: S22

23 1 H NMR spectrum of substrate 1e: 1 H NMR spectrum of product 2e: S23

24 13 C NMR spectrum of product 2e: S24

25 1 H NMR spectrum of substrate 1f: 1 H NMR spectrum of product 2f: S25

26 13 C NMR spectrum of product 2f: S26

27 1 H NMR spectrum of substrate 1g: 1 H NMR spectrum of product 2g: S27

28 13 C NMR spectrum of product 2g: S28

29 1 H NMR spectrum of substrate 1h: 1 H NMR spectrum of product 2h: S29

30 13 C NMR spectrum of product 2h: S30

31 1 H NMR spectrum of substrate 1i: Me Me Me N Me 1 H NMR spectrum of product 2i: S31

32 13 C NMR spectrum of product 2i: S32

33 1 H NMR spectrum of substrate 1j: 1 H NMR spectrum of product 2j: S33

34 13 C NMR spectrum of product 2j: S34

35 1 H NMR spectrum of substrate 1k: 1 H NMR spectrum of product 2k: S35

36 13 C NMR spectrum of product 2k: S36

37 1 H NMR spectrum of substrate 1l: 1 H NMR spectrum of product 2l: Br Me D(95%) Me N Me D(95%) S37

38 13 C NMR spectrum of product 2l: Br Me D(95%) Me N Me D(95%) S38

39 1 H NMR spectrum of substrate 1m: 1 H NMR spectrum of product 2m: S39

40 13 C NMR spectrum of product 2m: S40

41 1 H NMR spectrum of substrate 1n: 1 H NMR spectrum of product 2n: S41

42 13 C NMR spectrum of product 2n: S42

43 1 H NMR spectrum of substrate 1o: 1 H NMR spectrum of product 2o: S43

44 13 C NMR spectrum of product 2o: S44

45 1 H NMR spectrum of substrate 1p: 1 H NMR spectrum of product 2p: S45

46 13 C NMR spectrum of product 2p: S46

47 1 H NMR spectrum of substrate 1q: 1 H NMR spectrum of product 2q: S47

48 13 C NMR spectrum of product 2q: S48

49 1 H NMR spectrum of substrate 1r: 1 H NMR spectrum of product 2r: S49

50 13 C NMR spectrum of product 2r: S50

51 1 H NMR spectrum of substrate 1s: 1 H NMR spectrum of product 2s: S51

52 13 C NMR spectrum of product 2s: S52

53 1 H NMR spectrum of substrate 1t: 1 H NMR spectrum of product 2t: S53

54 13 C NMR spectrum of product 2t: S54

55 1 H NMR spectrum of substrate 1u: 1 H NMR spectrum of product 2u: S55

56 13 C NMR spectrum of product 2u: S56

57 1 H NMR spectrum of substrate 1v: 1 H NMR spectrum of product 2v: S57

58 13 C NMR spectrum of product 2v: S58

59 1 H NMR spectrum of substrate Melatonin 3: 1 H NMR spectrum of product 4: S59

60 13 C NMR spectrum of product 4: (91%) D MeO D (91%) N H HN O D (83%) S60

61 1 H NMR spectrum of product 1a: 1 H NMR spectrum of product 1p: S61

62 1 H NMR spectrum of product 1u: S62

63 8. Reference (1) M. Zhan, H. Jiang, X. Pang, T. Zhang, R. Xu, L. Zhao, Y. Liu, Y. Gong, Y. Chen, Tetrahedron Lett. 2014, 55, (2) L. Leseurre, C.-M. Chao, T. Seki, E. Genin, P. Y. Toullec, J.-P. Genêt, V. Michelet, Tetrahedron 2009, 65, (3) J. E. Taylor, M. D. Jones, J. M. J. Williams, S. D. Bull, Org. Lett. 2010, 12, (4) G. F. Kolar, J. Labelled. Compd. 1971, 7, S63

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