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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 206 Supporting information: A highly efficient heterogeneous copper-catalyzed Chan- Lam coupling reaction of sulfonyl azides with arylboronic acids leading to N-arylsulfonamides Chongren You a, Fang Yao b, Tao Yan a and Mingzhong Cai a * a Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang , P. R. China b College of Chemical and Material Engineering, Quzhou University, Quzhou , P. R. China Fax: (+86) ; mzcai@jxnu.edu.cn The spectral data of N-arylsulfonamides 3a-3c': 4-Methyl-N-phenylbenzenesulfonamide 3a. White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.69 (d, J = 8.0 Hz, 2H), (m, 5H), (m, 3H), 2.36 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.9, 36.6, 36.0, 29.7, 29.3, 27.3, 25.2, 2.4, Methyl-N-(p-tolyl)benzenesulfonamide 3b. White solid, mp 6-7 C. H NMR (400 MHz, CDCl 3 ): δ 7.65 (d, J = 8.0 Hz, 2H), 7.20 (d, J = 7.6 Hz, 2H), (m, 5H), 2.36 (s, 3H), 2.26 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.7, 36., 35.3, 33.8, 29.8, 29.6, 27.3, 22.2, 2.5, N-(4-Methoxyphenyl)-4-methylbenzenesulfonamide 3c. White solid, mp 3-4
2 C. H NMR (400 MHz, CDCl 3 ): δ 7.6 (d, J = 8.0 Hz, 2H), 7.9 (d, J = 8.0 Hz, 2H), 7.0 (s, H), 6.99 (d, J = 9.2 Hz, 2H), 6.73 (d, J = 8.8 Hz, 2H), 3.73 (s, 3H), 2.36 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 57.8, 43.7, 36.0, 29.6, 29., 27.3, 25.2, 4.4, 55.4, 2.5. N-(4-Chlorophenyl)-4-methylbenzenesulfonamide 3d. Pale yellow solid, mp 8-9 C. H NMR (400 MHz, CDCl 3 ): δ 7.68 (d, J = 8.4 Hz, 2H), 7.49 (s, H), 7.23 (d, J = 8.4 Hz, 2H), 7.7 (d, J = 8.8 Hz, 2H), 7.04 (d, J = 8.8 Hz, 2H), 2.37 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 44.2, 35.6, 35.2, 30.8, 29.8, 29.4, 27.3, 22.8, 2.6. N-(4-Bromophenyl)-4-methylbenzenesulfonamide 3e. 2 Pale yellow solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.73 (s, H), 7.70 (d, J = 7.6 Hz, 2H), 7.29 (d, J = 8.0 Hz, 2H), 7.2 (d, J = 8.0 Hz, 2H), 6.99 (d, J = 8.0 Hz, 2H), 2.35 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 44.2, 35.9, 35.7, 32.3, 29.8, 27.3, 22.9, 8.3, 2.6. N-(4-Fluorophenyl)-4-methylbenzenesulfonamide 3f. White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.65 (d, J = 6.8 Hz, 2H), 7.44 (m, H), 7.22 (d, J = 7.6 Hz, 2H), 7.07 (m, 2H), 6.9 (t, J = 7.6 Hz, 2H), 2.37 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 60.8 (d, J C-F = Hz), 44., 35.6, 32.4 (d, 4 J C-F = 2.2 Hz), 29.7, 27.3, 22.4 (d, 3 J C-F = 8.4 Hz), 6. (d, 2 J C-F = 22.6 Hz), 2.6. Anal. Calcd. for C 3 H 2 FNO 2 S: C, 58.85; H, 4.56; N, 5.28; S, Found: C, 58.59; H, 4.37; N, 5.45; S,.84. N-(Biphenyl-4-yl)-4-methylbenzenesulfonamide 3g. White solid, mp C. 2
3 H NMR (400 MHz, CDCl 3 ): δ 7.73 (d, J = 7.6 Hz, 2H), 7.49 (d, J = 7.6 Hz, 2H), 7.44 (d, J = 8.4 Hz, 2H), (m, 3H), 7.30 (t, J = 7.2 Hz, H), 7.22 (d, J = 7.6 Hz, 2H), 7.6 (d, J = 8.0 Hz, 2H), 2.35 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 44.0, 40., 38., 36.2, 35.9, 29.7, 28.8, 27.9, 27.4, 27.3, 26.8, 2.7, 2.5. Anal. Calcd. for C 9 H 7 NO 2 S: C, 70.56; H, 5.30; N, 4.33; S, 9.9. Found: C, 70.37; H, 5.48; N, 4.6; S, N-(3-Methoxyphenyl)-4-methylbenzenesulfonamide 3h. 3 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.73 (d, J = 8.0 Hz, 2H), 7.65 (s, H), 7.9 (d, J = 8.0 Hz, 2H), 7.08 (t, J = 8.4 Hz, H), 6.73 (s, H), 6.67 (d, J = 7.6 Hz, H), 6.59 (d, J = 8.4 Hz, H), 3.69 (s, 3H), 2.33 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 60.2, 43.9, 38.0, 36.0, 30.0, 29.7, 27.3, 3., 0.7, 06.6, 55.3, 2.5. N-(3,5-Dimethylphenyl)-4-methylbenzenesulfonamide 3i. 3 White solid, mp 90-9 C. NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J = 7.6 Hz, 2H), 7.26 (s, H), 7.2 (d, J = 7.6 Hz, 2H), 6.72 (s, 2H), 6.70 (s, H), 2.35 (s, 3H), 2.9 (s, 6H); 3 C NMR (00 MHz, CDCl 3 ): δ43.7, 39.0, 36.5, 36.3, 29.6, 27.3, 26.8, 8.8, 2.5, Methyl-N-(4-vinylphenyl)benzenesulfonamide 3j. 3 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.65 (d, J = 6.4 Hz, 2H), (m, 4H), 7.02(d, J = 6.4 Hz, 2H), (m, 2H), 5.66 (d, J = 6.8 Hz, H), 5.20 (d, J = 0.8 Hz, H), 2.38 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 44.0, 36.0, 35.9, 35.8, 34.8, 29.7, 27.3, 27.2, 2.6, 3.8, Methyl-N-(o-tolyl)benzenesulfonamide 3k. White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.62 (d, J = 8.0 Hz, 2H), 7.3 (d, J = 8.0 Hz, H), 7.2 (d, 3
4 J = 8.0 Hz, 2H), (m, 3H), 6.6 (s, H), 2.38 (s, 3H), 2.0 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.8, 36.7, 34.5, 3.4, 30.8, 29.6, 27.2, 26.9, 26.2, 24.3, 2.5, 7.6. N-(2-Methoxyphenyl)-4-methylbenzenesulfonamide 3l. 2 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.64 (d, J = 8.0 Hz, 2H), 7.52 (d, J = 8.0 Hz, H), 7.8 (d, J = 8.0 Hz, 2H), (m, 2H), 6.89 (t, J = 7.6 Hz, H), 6.73 (d, J = 8.0 Hz, H), 3.64 (s, 3H), 2.35 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 49.4, 43.6, 36.3, 29.3, 27.3, 26.0, 25.2, 2., 2.0, 0.6, 55.6, Methyl-N-(naphthalen--yl)benzenesulfonamide 3m. White solid, mp 4-42 C. H NMR (400 MHz, CDCl 3 ): δ 7.88 (d, J = 7.6 Hz, H), 7.78 (d, J = 6.8 Hz, H), (m, 3H), (m, 5H), 7.3 (d, J = 8.0 Hz, 2H), 2.3 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.8, 36.4, 34.2, 3.5, 29.6, 28.9, 28.4, 27.4, 27., 26.6, 26.3, 25.4, 22.6, 2.6, Methyl-N-(naphthalen-2-yl)benzenesulfonamide 3n. 3 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ (m, 5H), 7.6 (s, H), 7.56 (s, H), (m, 2H), 7.26 (d, J = 8.8 Hz, H), 7.6 (d, J = 7.6 Hz, 2H), 2.30 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 44.0, 35.9, 34.2, 33.7, 3.0, 29.8, 29.4, 27.7, 27.5, 27.3, 26.7, 25.5, 20.9, 8., Methyl-N-(thiophen-3-yl)benzenesulfonamide 3o. 3 White solid, mp 0- C. H NMR (400 MHz, CDCl 3 ): δ 7.67 (d, J = 8.0 Hz, 2H), 7.23 (d, J = 7.6 Hz, 2H), 7.6 (t, J = 4.0 Hz, H), 7.09 (s, H), (m, 2H), 2.38 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.9, 36.0, 34.3, 29.6, 27.3, 25.6, 23.3, 3.9,
5 N-Phenylmethanesulfonamide 3p. 4 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.35 (t, J = 8.0 Hz, 2H), 7.24 (d, J = 8.0 Hz, 2H), 7.9 (t, J = 7.4 Hz, H), 6.97 (s, H), 3.0 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 36.9, 29.7, 25.4, 20.9, N-p-Tolylmethanesulfonamide 3q. 4 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.5 (s, 4H), 7.00 (s, H), 2.98 (s, 3H), 2.33 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 35.6, 34.0, 30.2, 2.6, 38.9, N-(4-Methoxyphenyl)methanesulfonamide 3r. 5 White solid, mp 3-4 C. H NMR (400 MHz, CDCl 3 ): δ 7.22 (d, J = 8.8 Hz, 2H), 6.93 (br, H), 6.88 (d, J = 8.8 Hz, 2H), 3.80 (s, 3H), 2.96 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 58.0, 29.2, 24.7, 4.8, 55.5, N-(4-Chlorophenyl)methanesulfonamide 3s. 5 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.32 (d, J = 8.8 Hz, 2H), 7.8 (d, J = 8.4 Hz, 2H), 6.88 (br, H), 3.0 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 35.2, 3., 29.8, 22.2, Methoxy-N-phenylbenzenesulfonamide 3t. 6 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.74 (d, J = 8.8 Hz, 2H), 7.29 (br, H), 7.22 (t, J = 8.0 Hz, 2H), (m, 3H), 6.88 (d, J = 8.4 Hz, 2H), 3.80 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 63., 36.7, 30.5, 29.5, 29.3, 25.2, 2.4, 4.2, Methoxy-N-(4-methoxyphenyl)benzenesulfonamide 3u. 6 White solid, mp 00-0 C. H NMR (400 MHz, CDCl 3 ): δ 7.65 (d, J = 9.2 Hz, 2H), 6.99 (d, J = 8.8 Hz, 2H), 6.87 (d, J = 8.8 Hz, 2H), 6.84 (br, H), 6.75 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H), 5
6 3.75 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 63.0, 57.8, 30.5, 29.5, 29., 25.3, 4.4, 4., 55.6, N-(4-Chlorophenyl)-4-methoxybenzenesulfonamide 3v. White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.73 (d, J = 8.8 Hz, 2H), 7.47 (s, H), 7.8 (d, J = 8.8 Hz, 2H), 7.04 (d, J = 8.4 Hz, 2H), 6.89 (d, J = 8.4 Hz, 2H), 3.82 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 63.3, 35.3, 30.7, 30.0, 29.5, 29.4, 22.8, 4.3, Anal. Calcd. for C 3 H 2 ClNO 3 S: C, 52.44; H, 4.06; N, 4.70; S, Found: C, 52.57; H, 4.25; N, 4.53; S, Nitro-N-phenylbenzenesulfonamide 3w. 7 Yellow solid, mp C. H NMR (400 MHz, DMSO): δ 0.60 (s, H), 8.38 (d, J = 8.4 Hz, 2H), 8.02 (d, J = 8.4 Hz, 2H), 7.27 (t, J = 7.4 Hz, 2H), 7.3 (d, J = 7.6 Hz, 2H), 7.09 (t, J = 7.2 Hz, H); 3 C NMR (00 MHz, DMSO): δ 50.3, 45.4, 37.4, 29.8, 28.7, 25.2, 25., Nitro-N-(p-tolyl)benzenesulfonamide 3x. 7 Yellow solid, mp C. H NMR (400 MHz, DMSO): δ 0.42 (br, H), 8.36 (d, J = 8.8 Hz, 2H), 7.97 (d, J = 8.8 Hz, 2H), 7.05 (d, J = 8.4 Hz, 2H), 6.99 (d, J = 8.4 Hz, 2H), 2,8 (s, 3H); 3 C NMR (00 MHz,DMSO): δ 50.2, 45.5, 34.7, 34.6, 30.2, 28.7, 25.0, 2.8, N-(4-Methoxyphenyl)-4-nitrobenzenesulfonamide 3y. 7 Yellow solid, mp C. H NMR (400 MHz, DMSO): δ 0.23 (s, H), 8.37 (d, J = 8.4 Hz, 2H), 7.93 (d, J = 8.4 Hz, 2H), 7.00 (d, J = 8.4 Hz, 2H), 6.83 (d, J = 8.0 Hz, 2H), 3.68 (s, 3H); 3 C NMR (00 MHz, DMSO): δ 57.5, 50.2, 45.4, 29.7, 28.8, 25.0, 24.6, 4.9, N-(4-Chlorophenyl)-4-nitrobenzenesulfonamide 3z. 7 Yellow solid, mp C. 6
7 H NMR (400 MHz, DMSO): δ 0.74 (br, H), 8.39 (d, J = 6.8 Hz, 2H), 8.00 (d, J = 6.8 Hz, 2H), 7.33 (d, J = 6.8 Hz, 2H), 7.3 (d, J = 6.8 Hz, 2H); 3 C NMR (00 MHz, DMSO): δ 50.4, 45.0, 36.4, 29.8, 29.5, 28.7, 25.2, N-Phenylnaphthalene-2-sulfonamide 3a'. White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 8.4 (s, H), (m, 4H), (m, 2H), 7.50 (s, H), (m, 4H), 7.05 (t, J = 7.2 Hz, H); 3 C NMR (00 MHz, CDCl 3 ): δ 36.4, 35.9, 34.9, 32.0, 29.5, 29.4, 29.3, 29.0, 27.9, 27.6, 25.4, 22.3, 2.6. Anal. Calcd. for C 6 H 3 NO 2 S: C, 67.82; H, 4.62; N, 4.94; S,.32. Found: C, 67.58; H, 4.35; N, 4.67; S,.4. N-(4-Methoxyphenyl)naphthalene-2-sulfonamide 3b'. Yellow liquid. H NMR (400 MHz, CDCl 3 ): δ 8.29 (s, H), (m, 3H), 7.72 (dd, J = 8.6,.8 Hz, H), (m, 2H), 7.00 (d, J = 8.8 Hz, 2H), 6.86 (s, H), 6.72 (d, J = 8.8 Hz, 2H), 3.72 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 58., 36.0, 34.9, 32., 29.3, 29.2, 28.9, 28.7, 27.9, 27.5, 25.7, 22.5, 4.5, Anal. Calcd. for C 7 H 5 NO 3 S: C, 65.6; H, 4.82; N, 4.47; S, Found: C, 65.28; H, 4.57; N, 4.25; S, N-(4-Fluorophenyl)naphthalene-2-sulfonamide 3c'. White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 8.34 (s, H), (m, 3H), 7.77 (dd, J = 8.8,.6 Hz, H), (m, 2H), 7.43 (s, H), (m, 2H), 6.88 (t, J = 8.6 Hz, 2H); 3 C NMR (00 MHz, CDCl 3 ): δ 60.8 (d, J C-F = 250. Hz), 35.7, 35.5, 35.0, 32. (d, J C-F = 9.6 Hz), 29.5, 29.3, 29., 29.0, 27.9, 27.7, 24.7 (d, J C-F = 8.5 Hz), 22.2, 6.2 (d, J C-F = 22.5 Hz). Anal. Calcd. for C 6 H 2 FNO 2 S: C, 63.77; H, 4.0; N, 4.65; S, Found: C, 63.53; H, 3.88; N, 4.4; S,
8 4-Chloro-N-phenylbenzenesulfonamide 3d'. 3 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.72 (d, J = 8.4 Hz, 2H), 7.39 (d, J = 8.4 Hz, 2H); (m, 3H), (m, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 39.7, 37.4, 36., 29.5, 29.4, 28.7, 25.8, Chloro-N-(4-chlorophenyl)benzenesulfonamide 3e'. White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J = 8.8 Hz, 2H), 7.42 (d, J = 8.8 Hz, 2H), 7.28 (s, H), 7.22 (d, J = 8.8 Hz, 2H), 7.03 (d, J = 8.8 Hz, 2H); 3 C NMR (00 MHz, CDCl 3 ): δ 40.0, 37.0, 34.6, 3.5, 29.6, 29.5, 28.7, Anal. Calcd. for C 2 H 9 Cl 2 NO 2 S: C, 47.70; H, 3.00; N, 4.64; S, 0.6. Found: C, 47.43; H, 3.; N, 4.39; S, Chloro-N-(4-methoxyphenyl)benzenesulfonamide 3f'. White solid, mp 4-42 C. H NMR (400 MHz, CDCl 3 ): δ 7.64 (d, J = 8.4 Hz, 2H), 7.39 (d, J = 8.4 Hz, 2H), 6.99 (d, J = 8.8 Hz, 2H), 6.93 (s, H), 6.77 (d, J = 8.8 Hz, 2H), 3.76 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 58.2, 39.4, 37.4, 29.3, 28.8, 28.4, 25.7, 4.6, Anal. Calcd. for C 3 H 2 ClNO 3 S: C, 52.44; H, 4.06; N, 4.70; S, Found: C, 52.23; H, 3.79; N, 4.56; S, Methyl-6H-dibenzo[c,e][,2]thiazine 5,5-dioxide 4a. 3 White solid, mp C. H NMR (400 MHz, CDCl 3 ): δ 7.99 (d, J = 8.0 Hz, H), 7.89 (d, J = 8.0 Hz, H), 7.78 (s, H), (m, 2H), (m, H), 7.23 (br, H), 7.2 (d, J = 8.0 Hz, H), 2.52 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43., 35.6, 32.4, 32.3, 30.2, 29., 25.8, 25.3, 25.0, 23.0, 22., 20.6,
9 References W. Zhang, J. Xie, B. Rao and M. Luo, J. Org. Chem., 205, 80, Y.-C. Teo and F.-F. Yong, Synlett, 20, S.-Y. Moon, J. Nam, K. Rathwell and W.-S. Kim, Org. Lett., 204, 6, R. Lis and A. J. Marisca, J. Org. Chem., 987, 52, B. R. Rosen, J. C. Ruble, T. J. Beauchamp and A. Navarro, Org. Lett., 20, 3, T. Kato, I. Okamoto, A. Tanatani, T. Hatano, M. Uchiyama, H. Kagechika, H. Masu, K. Katagiri, M. Tominaga, K. Yamaguchi and I. Azumaya, Org. Lett., 2006, 8, A. L. Pera, A. Leggio and A. Liguori, Tetrahedron, 2006, 62,
10 H NMR and 3 C NMR spectra of compounds 3a-3f' and 4a. 0
11 H NMR and 3 C NMR spectra of compound 3a
12 H NMR and 3 C NMR spectra of compound 3b 2
13 H NMR and 3 C NMR spectra of compound 3c 3
14 H NMR and 3 C NMR spectra of compound 3d 4
15 H NMR and 3 C NMR spectra of compound 3e 5
16 H NMR and 3 C NMR spectra of compound 3f 6
17 H NMR and 3 C NMR spectra of compound 3g 7
18 H NMR and 3 C NMR spectra of compound 3h 8
19 H NMR and 3 C NMR spectra of compound 3i 9
20 H NMR and 3 C NMR spectra of compound 3j 20
21 H NMR and 3 C NMR spectra of compound 3k 2
22 H NMR and 3 C NMR spectra of compound 3l 22
23 H NMR and 3 C NMR spectra of compound 3m 23
24 H NMR and 3 C NMR spectra of compound 3n 24
25 H NMR and 3 C NMR spectra of compound 3o 25
26 H NMR and 3 C NMR spectra of compound 3p 26
27 H NMR and 3 C NMR spectra of compound 3q 27
28 H NMR and 3 C NMR spectra of compound 3r 28
29 H NMR and 3 C NMR spectra of compound 3s 29
30 H NMR and 3 C NMR spectra of compound 3t 30
31 H NMR and 3 C NMR spectra of compound 3u 3
32 H NMR and 3 C NMR spectra of compound 3v 32
33 H NMR and 3 C NMR spectra of compound 3w 33
34 H NMR and 3 C NMR spectra of compound 3x 34
35 H NMR and 3 C NMR spectra of compound 3y 35
36 H NMR and 3 C NMR spectra of compound 3z 36
37 H NMR and 3 C NMR spectra of compound 3a' 37
38 H NMR and 3 C NMR spectra of compound 3b' 38
39 H NMR and 3 C NMR spectra of compound 3c' 39
40 H NMR and 3 C NMR spectra of compound 3d' 40
41 H NMR and 3 C NMR spectra of compound 3e' 4
42 H NMR and 3 C NMR spectra of compound 3f' 42
43 H NMR and 3 C NMR spectra of compound 4a 43
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