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1 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 with amines in aqueous medium at room temperature Xiaojun Pan, Jian Gao, Juan Liu, Junyi Lai, Huanfeng Jiang and Gaoqing Yuan* chool of Chemistry and Chemical Engineering, outh China University of Technology, Guangzhou 50640, China gqyuan@scut.edu.cn Table of Contents General Information...2 Typical procedure for the synthesis of sulfonamides...2 Analytical data of the prepared compounds...2 NMR spectra of the prepared compounds...9
2 General Information The H NMR and 3 C NMR spectra were recorded on a Bruker Advance 400 spectrometer in CDCl 3 at 400 MHz and 00 MHz, respectively. The chemical shifts were referenced to signals at 7.26 and 77.0 ppm, respectively. Proton coupling patterns were described as singlet (s), doublet (d), triplet (t), quartet (q) and multiplet (m). Mass spectra were recorded on a himadzu GCM- QP5050A spectrometer at an ionization voltage of 70 ev equipped with a DB-WAX capillary column (internal diameter: 0.25 mm, length: 30 m). GC-M was obtained using electron ionization. High resolution mass spectra (HRM) were recorded on a MAT95XP high resolution mass spectrometer. TLC was performed using commercially prepared mesh silica gel plates (GF254), and visualization was effected at 254 nm. All substrates were purchased commercially without further purification. Typical procedure for the synthesis of sulfonamides The mixture of iodine (0.25 mmol), sodium sulfinates (0.6 mmol), water (2 ml) and amines (0.5 mmol) were added to a 0 ml tube successively. Then, the reaction was performed at room temperature under magnetic stirring for 3 h. When it was finished, some ethyl acetate was added to the tube to extract the aqueous solution. After extracting, the obtained organic layer was dried with anhydrous Mg 4. The solvent was removed under vacuum, and the crude residue was purified by silica gel column chromatography to afford the desired pure product. Analytical Data of the prepared compounds N N-Benzyl-N,4-dimethylbenzenesulfonamide (3a) H NMR (400 MHz, CDCl 3 ): δ 7.73 (d, J =7.7Hz, 2H), (m, 7H), 4.2 (s, 2H), 2.58 (s, 3H), 2.45 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.4, 35.7, 34.3, 29.7, 28.6, 28.3, 27.8, 27.5, 54., 34.3, 2.5; M (EI) m/z: 275, 98, 84, 55, 20, 9. 2
3 NH 4-Methyl-N-(thiophen-2-ylmethyl)benzenesulfonamide (3b) 2 H NMR (400 MHz, CDCl 3 ): δ 7.77 (d, J =7.5 Hz, 2H), 7.32 (d, J =7.7 Hz, 2H), 7.20 (d, J =4.6 Hz, H), 6.88 (d, J =5.5 Hz, 2H), 5.8 (t, J =5.4 Hz, H), 4.34 (d, J =6.0 Hz, 2H), 2.45 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.5, 39.0, 36.7, 29.6, 27., 26.8, 26.4, 25.6, 4.9, 2.4; M (EI) m/z: 267, 207, 39, 2, 9. NH N-(Furan-2-ylmethyl)-4-methylbenzenesulfonamide (3c) 3 H NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J =7.6 Hz, 2H), 7.25 (d, J =7.8 Hz, 2H), 7.2 (s, H), 6.9 (s, H), 6.08 (s, H), 5.8 (br, H), 4.4 (d, J =5.8 Hz, 2H), 2.40 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 49.6, 43.3, 42.3, 36.8, 29.5, 27.0, 0.3, 08., 40.0, 2.4; M (EI) m/z: 25, 86, 55, 39, 96. H N 4-Methyl-N-phenylbenzenesulfonamide (3d) H NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J =8.2 Hz, 2H), 7.59 (br, H), (m, 7H), 2.32 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.8, 36.6, 35.9, 29.6, 29.2, 27.2, 25.0, 2.2, 2.4; M (EI) m/z: 247, 82, 68, 55, 9. NH N-Benzyl-4-methylbenzenesulfonamide (3e ) H NMR (400 MHz, CDCl 3 ): δ 7.75 (d, J =7.7 Hz, 2H), (m, 7H), 4.79 (br, H), 4. (d, J =5.9 Hz, 2H), 2.43 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.4, 36.8, 36.3, 29.6, 28.6, 27.8, 27.7, 27., 47., 2.4; M (EI) m/z: 26, 96, 55, 06, 9. 3
4 F NH N-(4-Fluorobenzyl)-4-methylbenzenesulfonamide (3e 2 ) 4 H NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J =7.6 Hz, 2H), 7.27 (d, J =7.6 Hz, 2H), (m, 2H), (m, 2H), 5.24 (t, J =5.6 Hz, H), 4.06 (d, J =6. Hz, 2H), 2.42 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 63.4, 6.0, 43.5, 36.8, 32.2, 29.7, 29.6, 29.5, 27.0, 5.5, 5.3, 46.4, 2.4; M (EI) m/z: 279, 24, 55, 24, 9. Cl NH N-(4-Chlorobenzyl)-4-methylbenzenesulfonamide (3e 3 ) 4 H NMR (400 MHz, CDCl 3 ): δ 7.69 (d, J =7.5 Hz, 2H), 7.25 (d, J =7.8 Hz, 2H), 7.8 (d, J =7.4 Hz, 2H), 7.0 (d, J =7.8 Hz, 2H), 5.42 (br, H), 4.04 (d, J =6.3 Hz, 2H), 2.4 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.5, 36.7, 34.9, 33.4, 29.6, 29.2, 28.6, 27.0, 46.4, 2.4; M (EI) m/z: 295, 230, 40, 25, 9. Br NH N-(4-Bromobenzyl)-4-methylbenzenesulfonamide (3e 4 ) 4 H NMR (400 MHz, CDCl 3 ): δ 7.69 (d, J =8.0 Hz, 2H), 7.33 (d, J =8. Hz, 2H), 7.25 (d, J = 7.7 Hz, 2H), 7.05 (d, J =8.0 Hz, 2H), 5.37 (br, H), 4.03 (d, J =4.2 Hz, 2H), 2.42 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.6, 36.7, 35.5, 3.6, 29.7, 29.5, 27.0, 2.6, 46.4, 2.4; M (EI) m/z: 339, 207, 84, 57, 9. NH 4-Methyl-N-(4-methylbenzyl)benzenesulfonamide (3e 5 ) 4 4
5 H NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J =7.7 Hz, 2H), 7.24 (d, J =7.7Hz, 2H), (m, 4H), 5.8 (br, H), 4.0 (d, J =6.0 Hz, 2H), 2.39 (s, 3H), 2.26 (s, 3H); 3 C NMR (00MHz, CDCl 3 ): δ 43.2, 37.3, 36.8, 33.2, 29.5, 29., 27.7, 27.0, 46.8, 2.3, 20.9; M (EI) m/z: 275, 20, 39, 20, 9. NH N-(4-Methoxybenzyl)-4-methylbenzenesulfonamide (3e 6 ) 5 H NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J =7.4 Hz, 2H), 7.25 (d, J =7.3 Hz, 2H), 7.08 (d, J =7.4 Hz, 2H), 6.75 (d, J =7.4 Hz, 2H), 5.22 (br, H), 4.00 (d, J =3.8 Hz, 2H), 3.73 (s, 3H), 2.40 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 59.0, 43.2, 36.8, 29.5, 29., 28.3, 27.0, 3.8, 55., 46.5, 2.3; M (EI) m/z: 29, 55, 35, 2, 9. N N,4-Dimethyl-N-phenylbenzenesulfonamide (3f ) H NMR (400 MHz, CDCl 3 ): δ 7.43 (d, J =7.8 Hz, 2H), (m, 5H), 7.0 (d, J =7.6 Hz, 2H), 3.6 (s, 3H), 2.4(s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.5, 4.6, 33.6, 29.3, 28.8, 27.9, 27.2, 26.6, 38., 2.5; M (EI) m/z: 26, 97, 55, 06, 9, 77. N Br N-(4-Bromophenyl)-N,4-dimethylbenzenesulfonamide (3f 2 ) H NMR (400 MHz, CDCl 3 ): δ 7.40 (d, J =8.5 Hz, 4H), 7.24 (d, J =7.7 Hz, 2H), 6.97 (d, J =7.3 Hz, 2H), 3.2 (s, 3H), 2.4 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.8, 40.6, 32.9, 3.8, 29.4, 28.0, 27.7, 20.8, 37.8, 2.4; M (EI) m/z: 340, 96, 55, 05, 9; HRM (EI) m/z: calcd for C 4 H 4 BrNNa 2 [M+Na]+, ; found NH N,4-Dimethylbenzenesulfonamide (3g ) 5
6 H NMR (400 MHz, CDCl 3 ): δ 7.77 (d, J =8.Hz, 2H), 7.33 (d, J =8.0 Hz, 2H), 4.65 (br, H), 2.65 (d, J =5.0 Hz, 3H), 2.45 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.5, 35.8, 29.7, 27.2, 29.3, 2.5; M (EI) m/z: 85, 55, 2, 9. NH 4-Methyl-N-propylbenzenesulfonamide (3g 2 ) H NMR (400 MHz, CDCl 3 ): δ 7.78 (d, J =7.7 Hz, 2H), 7.33(d, J =7.7 Hz, 2H), 4.76 (br, H), (m, 2H), 2.45 (s, 3H), (m, 2H), 0.88 (t, J =7.4 Hz, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.3, 37.0, 29.6, 27.0, 44.9, 22.9, 2.4,.0; M (EI) m/z: 23, 84, 55, 9. H N N-Tert-butyl-4-methylbenzenesulfonamide (3g 3 ) H NMR (400 MHz, CDCl 3 ): δ 7.77 (d, J =8.2 Hz, 2H), 7.27 (d, J =8.3 Hz, 2H), 4.63 (br, H), 2.42 (s, 3H),.22 (s, 9H); 3 C NMR (00 MHz, CDCl 3 ): δ 42.8, 40.5, 29.4, 27.0, 54.6, 30., 2.4; M (EI) m/z: 227, 22, 55, 9. NH N-Hexyl-4-methylbenzenesulfonamide (3g 4 ) H NMR (400 MHz, CDCl 3 ): δ 7.75 (d, J =8. Hz, 2H), 7.30 (d, J =8.0 Hz, 2H), 4.57 (br, H), (m, 2H), 2.43 (s, 3H), (m, 2H), (m, 6H), 0.84 (t, J =6.7 Hz, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.3, 37.0, 29.6, 27., 43.2, 3.2, 29.5, 26., 22.4, 2.5, 3.9; M (EI) m/z: 255, 84, 55, 00, 9. NH N N-(2-(Dimethylamino)ethyl)-4-methylbenzenesulfonamide (3h) H NMR (400 MHz, CDCl 3 ): δ 7.76 (d, J =7.7 Hz, 2H), 7.3 (d, J =7.6 Hz, 2H), (m, 2H), 2.43 (s, 3H), (m, 2H), 2.09 (s, 6H),.26 (br, H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.3, 36.7, 29.6, 27., 57.0, 44.7, 40.0, 2.5; M (EI) m/z: 242, 23, 55, 48, 9; HRM (EI) m/z: calcd for C H 8 N 2 Na 2 [M+Na]+, ; found
7 H N N-Allyl-4-methylbenzenesulfonamide (3i) H NMR (400 MHz, CDCl 3 ): δ 7.78 (d, J =8.3 Hz, 2H), 7.33 (d, J =8.0 Hz, 2H), (m, H), (m, 2H), 4.55 (br, H), 3.6 (t, J = 6.0 Hz, 2H), 2.45 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.5, 37.0, 33.0, 29.7, 27., 7.7, 45.8, 2.5; M (EI) m/z: 2, 84, 55, 9. N N,N-Diethyl-4-methylbenzenesulfonamide (3j) H NMR (400 MHz, CDCl 3 ): δ 7.7 (d, J =7.6 Hz, 2H), 7.30 (d, J =8.0 Hz, 2H), 3.24 (q, J =7. Hz, 4H), 2.43 (s, 3H),.4 (t, J =7. Hz, 6H); 3 C NMR (00 MHz, CDCl 3 ): δ 42.9, 37.4, 29.5, 27.0, 42.0, 2.4, 4.; M (EI) m/z: 227, 84, 55, 9. N N N-(2-cyanoethyl)-N,4-dimethylbenzenesulfonamide (3k) H NMR (400 MHz, CDCl 3 ): δ 7.69 (d, J =7.7 Hz, 2H), 7.35 (d, J =7.8 Hz, 2H), 3.33 (t, J =6.8 Hz, 2H), 2.86 (s, 3H), 2.67 (t, J =6.8 Hz, 2H), 2.45 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 44.0, 34.0, 29.9, 27.2, 7.4, 46.3, 36.0, 2.4, 8.; M (EI) m/z: 238, 98, 55, 9; HRM (EI) m/z: calcd for C H 4 N 2 Na 2 [M+Na]+, ; found N -Tosylpyrrolidine (3l) H NMR (400 MHz, CDCl 3 ): δ 7.72 (d, J =8.0 Hz, 2H), 7.32 (d, J =8.0 Hz, 2H), 3.23 (t, J =6.6 Hz, 4H), 2.43 (s, 3H), (m, 4H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.2, 33.9, 29.5, 27.5, 47.8, 25., 2.4; M (EI) m/z: 225, 55, 9. N 4-Tosylmorpholine (3m) 7
8 H NMR (400 MHz, CDCl 3 ): δ 7.64 (d, J =8. Hz, 2H), 7.35 (d, J =8.0 Hz, 2H), 3.74(t, J =4.8 Hz, 4H), 2.98 (t, J =4.8 Hz, 4H), 2.44 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.9, 32.0, 29.7, 27.8, 66.0, 45.9, 2.5; M (EI) m/z: 24, 98, 55, 06, 9, 86. N 4-Tosylthiomorpholine (3n) 6 H NMR (400 MHz, CDCl 3 ): δ 7.64 (d, J =7.7 Hz, 2H), 7.35 (d, J =7.8 Hz, 2H), 3.34 (s, 4H), 2.72 (s, 4H), 2.46 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 43.7, 33.7, 29.8, 27.4, 47.8, 27.3, 2.5; M (EI) m/z: 257, 242, 93, 55, 02, 9. N N-Benzyl-N-methylbenzenesulfonamide (3o ) 7 H NMR (400 MHz, CDCl 3 ): δ 7.85 (d, J =7.6 Hz, 2H), (m, 3H), (m, 5H), 4.5 (s, 2H), 2.6 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 37.4, 35.5, 32.6, 29., 28.6, 28.3, 27.9, 27.4, 54., 34.3; M (EI) m/z: 26, 84, 4, 8, 9. F N N-Benzyl-4-fluoro-N-methylbenzenesulfonamide (3o 2 ) 7 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), (m, 7H), 4.5 (s, 2H), 2.6 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 66.3, 63.8, 35.3, 33.6, 30., 30.0, 28.6, 28.3, 27.9, 6.4, 6.2, 54.0, 34.2; M (EI) m/z: 279, 202, 20, 9. Cl N N-Benzyl-4-chloro-N-methylbenzenesulfonamide (3o 3 ) 7 8
9 H NMR (400 MHz, CDCl 3 ): δ 7.77 (d, J =7.9 Hz, 2H), 7.53 (d, J =8.0 Hz, 2H), (m, 5H), 4.5 (s, 2H), 2.6 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 39.2, 36.0, 35.2, 29.4, 28.8, 28.6, 28.3, 28.0, 54.0, 34.2; M (EI) m/z: 295, 28, 75, 20, 9. Br N N-Benzyl-4-bromo-N-methylbenzenesulfonamide (3o 4 ) 7 H NMR (400 MHz, CDCl 3 ): δ 7.70 (s, 4H), (m, 5H), 4.5 (s, 2H), 2.6 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 36.5, 35.2, 32.4, 28.9, 28.7, 28.3, 28.0, 27.6, 54.0, 34.3; M (EI) m/z: 339, 262, 55, 20, 9. 2-Tosylethene-,-diyldibenzene (4a) 8 H NMR (400 MHz, CDCl 3 ): δ 7.47 (d, J =8.2 Hz, 2H), (m, 2H), 7.29 (td, J =7.4,.6 Hz, 4H), (m, 2H), 7.4 (d, J =8. Hz, 2H), (m, 2H), 6.99 (s, H), 2.37 (s, 3H); 3 C NMR (00 MHz, CDCl 3 ): δ 54.6, 43.7, 39.2, 38.6, 35.5, 30.2, 29.7, 29.3, 28.9, 28.8, 28.5, 28., 27.7, 27.6, 2.5; M (EI) m/z: 334, 269, 78, 67, 39, 9. References. X. D. Tang, L. B. Huang, C. R. Qi, X. Wu, W. Q. Wu and H. F. Jiang, Chem. Commun. 203, 49, F. hi, M. K. Tse, X. J. Cui, D. Gördes, D. Michalik, K. Thurow, Y. Q. Deng and M. Beller, Angew. Chem., Int. Ed. 2009, 48, A. Kamal, J.. Reddy, E. V. Bharathi and D. Dastagiri, Tetrahedron Letters. 2008, 49, X. J. Cui, F. hi, Y. Zhang and Y. Q. Deng, Tetrahedron Letters. 200, 5, C. Z. Liu,. H. Liao, Q. Li,. L. Feng, Q. un, X. C. Yu and Q. Xu, J. rg. Chem. 20, 76, K. aruta, T. giku and K. Fukase, Tetrahedron Letters. 2009, 50, D. A. Powell and H. Fan, J. rg. Chem. 200, 75, D. C. Reeves,. Rodriguez, H. Lee, N. Haddad, D. Krishnamurthy and C. H. enanayake, Tetrahedron Letters. 2009, 50,
10 NMR spectra of the prepared compounds Fig. -. H-NMR spectrum of 3a. Fig C-NMR spectrum of 3a. 0
11 Fig. -3. H-NMR spectrum of 3b. Fig C-NMR spectrum of 3b.
12 Fig. -5. H-NMR spectrum of 3c. Fig C-NMR spectrum of 3c. 2
13 Fig. -7. H-NMR spectrum of 3d. Fig C-NMR spectrum of 3d. 3
14 Fig. -9. H-NMR spectrum of 3e. Fig C-NMR spectrum of 3e. 4
15 Fig. -. H-NMR spectrum of 3e 2. Fig C-NMR spectrum of 3e 2. 5
16 Fig. -3. H-NMR spectrum of 3e 3. Fig C-NMR spectrum of 3e 3. 6
17 Fig. -5. H-NMR spectrum of 3e 4. Fig C-NMR spectrum of 3e 4. 7
18 Fig. -7. H-NMR spectrum of 3e 5. Fig C-NMR spectrum of 3e 5. 8
19 Fig. -9. H-NMR spectrum of 3e 6. Fig C-NMR spectrum of 3e 6. 9
20 Fig. -2. H-NMR spectrum of 3f. Fig C-NMR spectrum of 3f. 20
21 Fig H-NMR spectrum of 3f 2. Fig C-NMR spectrum of 3f 2. 2
22 Fig H-NMR spectrum of 3g. Fig C-NMR spectrum of 3g. 22
23 Fig H-NMR spectrum of 3g 2. Fig C-NMR spectrum of 3g 2. 23
24 Fig H-NMR spectrum of 3g 3. Fig C-NMR spectrum of 3g 3. 24
25 Fig. -3. H-NMR spectrum of 3g 4. Fig C-NMR spectrum of 3g 4. 25
26 Fig H-NMR spectrum of 3h. Fig C-NMR spectrum of 3h. 26
27 Fig H-NMR spectrum of 3i. Fig C-NMR spectrum of 3i. 27
28 Fig H-NMR spectrum of 3j. Fig C-NMR spectrum of 3j. 28
29 Fig H-NMR spectrum of 3k. Fig C-NMR spectrum of 3k. 29
30 Fig. -4. H-NMR spectrum of 3l. Fig C-NMR spectrum of 3l. 30
31 Fig H-NMR spectrum of 3m. Fig C-NMR spectrum of 3m. 3
32 Fig H-NMR spectrum of 3n. Fig C-NMR spectrum of 3n. 32
33 Fig H-NMR spectrum of 3o. Fig C-NMR spectrum of 3o. 33
34 Fig H-NMR spectrum of 3o 2. Fig C-NMR spectrum of 3o 2. 34
35 Fig. -5. H-NMR spectrum of 3o 3. Fig C-NMR spectrum of 3o 3. 35
36 Fig H-NMR spectrum of 3o 4. Fig C-NMR spectrum of 3o 4. 36
37 Fig H-NMR spectrum of 4a. Fig C-NMR spectrum of 4a. 37
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