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1 Supporting Information 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions Xinxin Qi, [a] Li-Bing Jiang, [a] Chao Zhou, [a] Jin-Bao Peng, [a] [a, b] and Xiao-Feng Wu* open_ _sm_miscellaneous_information.pdf
2 Supporting Information 1. General procedure for the preparation of aryl diazonium tetrafluoroborates 1 Arylamine (10 mmol) was dissolved in a mixture of 5 ml of distilled water and 3.4mL of 50% hydrofluoroboric acid. After cooling the reaction mixture to 0 C using ice bath and the sodium nitrite (0.69 g in 2 ml distilled water) was added dropwise in 5 min interval of time. The resulting mixture was stirred for 1h and the precipitate was collected by filtration and redissolved in minimum amount of acetone. Diethylether was added until precipitation of aryl diazonium tetrafluoroborate, which is filtered, washed several times with diethyl ether and dried under vacuum 2. General procedure for the preparation of triazenes 2 Aryl amine (21 mmol) was added to 12 ml of 6 M HCl at 0 C, and then sodium nitrite (1.63 g, 23.6 mmol) in 6 ml of H 2 O was added dropwise. After stirring for 10 min, the mixture was added slowly to a solution of Et 2 NH (3.3 ml, 56.7 mmol) and K 2 CO 3 (4.5 g, 32 mmol) in ice water (30 ml). Stirring at room temperature for 0.5 hour and extracted with ethyl acetate (30 ml 3). The combined organic phase was dried over Na 2 SO 4 and the product was obtained by column chromatography. 3.Typical procedure for the borylation of aryldiazonium salts Aryldiazonium salts (1.0 mmol), bis(pinacolato)diboron (1.2 mmol), Zn(ClO 4 ) 2 (5 mol%) were added into a 15 ml Schlenk tube under nitrogen atmosphere. Then 4 ml CH 3 OH was added by a syringe. The mixture was stirred for 8-15 h at 40 C. After the reaction was completed, the reaction mixture was filtered, concentrated and column chromatography on silica gel (petroleum ether/ethyl acetate 50:1). 4.Typical procedure for the borylation of triazenes Triazenes (1 mmol), bis(pinacolato)diboron (1.2 mmol), Trifluoromethanesulfonic acid (1 mmol), Zn(ClO 4 ) 2 (5 mol%) were weighed in a 15 ml Schlenk tube under nitrogen atmosphere. Then 4 ml CH 3 OH was added by a syringe. The mixture was stirred for h at 60 C. After the reaction was complete, the reaction mixture was filtered, concentrated and column chromatography on silica gel (petroleum ether/ethyl acetate 50:1). 1
3 5.NMR data of products 4,4,5,5-Tetramethyl-2-phenyl-[1,3,2]dioxaborolane 3 1 H NMR (400 MHz, CDCl 3 ) δ 7.83 (d, J = 7.6 Hz, 2H), 7.47 (t, J = 7.2 Hz, 1H), 7.38 (t, J = 7.5 Hz, 2H), 1.36 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 83.68, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 13), (40), (73), (73), (100), 85.0 (18), 77.0 (10), 59.0 (10). 4,4,5,5-Tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane 3 1 H NMR (400 MHz, CDCl 3 ) δ 7.68 (d, J = 7.1 Hz, 1H), 7.21 (dd, J = 11.1, 3.7 Hz, 1H), 7.07 (dd, J = 7.1, 3.6 Hz, 2H), 2.45 (s, 3H), 1.24 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , 83.31, 24.83, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 13), (40), (50), (93), (100), 91.0 (14), 85.0 (12). 4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane 6 1 H NMR (400 MHz, CDCl 3 ) δ 7.55 (d, J = 4.3 Hz, 1H), (m, 1H), 7.18 (dd, J = 8.2, 4.1 Hz, 2H), 2.25 (d, J = 8.4 Hz, 3H), 1.25 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , 83.64, 24.84, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 13), (40), (45), (13), (90), (100), 91.0 (14), 85.0 (10). 2
4 4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane 3 1 H NMR (400 MHz, CDCl 3 ) δ 7.62 (d, J = 7.8 Hz, 2H), 7.09 (d, J = 7.8 Hz, 2H), 2.26 (s, 3H), 1.23 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 83.64, 24.87, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 13), (64), (70), (91), (100), 91.0 (14), 85.0 (10). 2-(4-(tert-Butyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 7 1 H NMR (400 MHz, CDCl 3 ) δ 7.83 (d, J = 8.1 Hz, 2H), 7.46 (d, J = 8.1 Hz, 2H), 1.38 (s, 12H), 1.37 (s, 9H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 83.51, 34.81, 31.15, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 14), (18), (100), (27), (32), (10), (14), (10). 2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5 1 H NMR (400 MHz, CDCl 3 ) δ 7.75 (d, J = 8.7 Hz, 2H), 6.89 (d, J = 8.7 Hz, 2H), 3.82 (s, 3H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 83.50, 55.01, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 12), (86), (58), (10), (64), (100), (13), 91.0 (13), 85.0 (12), 77.0 (12). 4,4,5,5-Tetramethyl-2-(4-(methylthio)phenyl)-1,3,2-dioxaborolane 6 3
5 1 H NMR (400 MHz, CDCl 3 ) δ 7.70 (d, J = 8.2 Hz, 2H), 7.21 (d, J = 8.2 Hz, 2H), 2.47 (s, 3H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 83.67, 24.81, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 12), (100), (34), (32), (96), (14), (14), 85.0 (12). 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 4 1 H NMR (400 MHz, CDCl 3 ) δ 7.69 (d, J = 8.4 Hz, 2H), 6.81 (d, J = 8.4 Hz, 2H), 6.62 (s, 1H), 1.34 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 83.87, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 12), (70), (70), (50), (100), 85.0 (15), 77.0 (15), 59.0 (12). 4,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane 3 1 H NMR (400 MHz, CDCl 3 ) δ 8.09 (d, J = 8.6 Hz, 2H), 7.87 (d, J = 8.5 Hz, 2H), 1.28 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 84.54, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 11), (13), (100), (15), (75), (43), (12), 85.0 (11), 58.0 (14). 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 4 1 H NMR (400 MHz, CDCl 3 ) δ 7.86 (d, J = 8.2 Hz, 2H), 7.62 (d, J = 8.3 Hz, 2H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , 84.42, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 12), (17), (100), (13), (10), (75), (45), 85.0 (10), 58.0 (11). 4
6 4,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 4 1 H NMR (400 MHz, CDCl 3 ) δ 7.90 (d, J = 7.7 Hz, 2H), 7.60 (d, J = 7.8 Hz, 2H), 1.35 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , (d), (d), (d), 84.25, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 14), (20), (100), (87), (87), (20), 85.0 (17), 58.0 (17). 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one 3 1 H NMR (400 MHz, CDCl 3 ) δ 7.91 (d, J = 8.2 Hz, 2H), 7.87 (d, J = 8.2 Hz, 2H), 2.59 (s, 3H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , 84.14, 26.72, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 13), (25), (100)202.9 (13), (15), (38), (63), (19),103.0 (10) Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 4 1 H NMR (400 MHz, CDCl 3 ) δ 7.99 (t, J = 6.1 Hz, 2H), 7.84 (d, J = 8.2 Hz, 2H), (m, 2H), (m, 3H), 1.32 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , 84.03, 60.91, 24.77, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 18), (25), (80), (43), (96), (100), (13), (30), (20), (20), 85.0 (15), 77.0 (13). 5
7 2-(4-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (dd, J = 8.3, 6.3 Hz, 2H), 7.04 (t, J = 8.9 Hz, 2H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ (d), (d), (d), 83.86, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 11), (37), (95), (18), (18), (64), (100), 85.0 (19), 59.0 (10). 2-(4-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 3 1 H NMR (400 MHz, CDCl 3 ) δ 7.73 (d, J = 8.3 Hz, 2H), 7.34 (d, J = 8.3 Hz, 2H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 84.02, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 14), (36), (86), (64), (100), (10), (13), 85.0 (25), 77.0 (20), 59.0 (20). 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5 1 H NMR (400 MHz, CDCl 3 ) δ 7.66 (d, J = 8.2 Hz, 2H), 7.50 (d, J = 8.2 Hz, 2H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 83.98, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 15), (50), (100), (72), (93), (14), (25), 85.0 (21), 77.0 (15), 59.0 (12). 2-(4-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6 1 H NMR (400 MHz, CDCl 3 ) δ 7.71 (d, J = 8.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H), 1.33 (s, 12H). 6
8 13 C NMR (101 MHz, CDCl 3 ) δ , , 98.82, 83.98, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 13), (100), (89), (89), (78), (12), (20), (31), 94.0 (20), 85.0 (22), 77.0 (20), 59.0 (20). 2-(2,6-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5 1 H NMR (400 MHz, CDCl 3 ) δ 7.63 (s, 2H), 7.42 (s, 1H), 1.33 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , 84.48, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 14),271.8 (43), (79), (100), (64), (15), 85.0 (22), 58.0 (22). 2-(2-Chloro-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5 1 H NMR (400 MHz, CDCl 3 ) δ 7.63 (d, J = 2.3 Hz, 1H), 7.18 (dd, J = 8.1, 2.4 Hz, 1H), 7.01 (d, J = 8.1 Hz, 1H), 2.41 (s, 3H), 1.26 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , 83.75, 24.84, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 10), (40), (40), (100), (14), (70),117.0 (34), 85.0 (12), 58.0 (11). 4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane 3 1 H NMR (400 MHz, CDCl 3 ) δ 8.79 (d, J = 8.5 Hz, 1H), 8.10 (d, J = 6.8 Hz, 1H), 7.95 (d, J = 8.1 Hz, 1H), 7.85 (d, J = 7.9 Hz, 1H), 7.55 (dd, J = 11.1, 4.1 Hz, 1H), (m, 2H), 1.44 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , 83.68, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 14), (78), (12), (12), (10), (34), (35), (100), (10). 7
9 2-([1,1'-Biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4 1 H NMR (400 MHz, CDCl 3 ) δ 7.88 (d, J = 8.0 Hz, 2H), (m, 4H), 7.43 (t, J = 7.5 Hz, 2H), 7.34 (t, J = 7.3 Hz, 1H), 1.35 (s, 12H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , 83.81, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 9), (80), (27), (11), (60), (100), (14). 2,2,6,6-Tetramethyl-1-(4-nitrophenoxy)piperidine 8 1 H NMR (400 MHz, CDCl 3 ) δ 8.04 (d, J = 8.1 Hz, 2H), 7.24 (s, 2H), 1.51 (s, 5H), 1.33 (s, 1H), 1.13 (s, 6H), 0.87 (s, 6H). 13 C NMR (101 MHz, CDCl 3 ) δ , , , , 60.39, 39.15, 31.76, 19.95, GC-MS (EI, 70 ev): m/z( % ) = ([M]+, 12),277.9 (14),194.7 (10), (13), (17), (30), 69.0 (100),58.0 (11). References: 1.P. Hanson, J. R. Jones, A. B. Taylor, P. H. Walton, A. W. Timms, J. Chem. Soc., Perkin Trans. 2002, 2, M. Kovac, M. Anderluh, J. Vercouillie, D. Guilloteau, P. Emond, S. Mavel, J. Fluorine Chem. 2013, 147, P. B. Dzhevakov, M. A. Topchiy, D. A. Zharkova, O. S. Morozov, A. F. Asachenko, M. S. Nechaev, Adv. Synth. Catal.2016, 358, K. Chen, S. Zhang, P. He, P. F. Li, Chem. Sci. 2016, 7, J. Yu, L. Zhang, G. Yan, Adv. Synth. Catal. 2012, 354, D. Qiu, L. Jin, Z. T. Zheng, H. Meng, F. Y. Mo, X. Wang, Y. Zhang, J. B. Wang, J. Org. Chem. 2013, 78, W. K. Chow, C. M. So, C. P. Lau, F. Y. Kwong, Chem. Eur. J. 2011, 17, M. D. Perretti, D. M. Monzón, F. P. Crisóstomo, V. S. Martín, R. Carrillo, Chem. Commun. 2016, 52,
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Electronic upplementary Material (EI) for Green Chemistry. This journal is The Royal ociety of Chemistry 204 upporting Information ynthesis of sulfonamides via I 2 -mediated reaction of sodium sulfinates
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Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
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