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4-Nitrobenzenesulfonamide (Table 2, entry 5): H NMR (90
MHz, DMSO-d6, CDCl3): d ¼ 8.27 (d, J ¼ 9.9 Hz, 2H), 8.00 (d, J ¼
9.9 Hz, 2H), 3.29 (s, 2H).
Acknowledgements
Authors gratefully wish to acknowledge the Iranian Nano
Council and Bu-Ali Sina University for their support to carry out
this research.
Typical procedure for the N-arylation of sulfonamides
To a mixture of Cu–zeolite (0.05 g) in water (10 mL), were added
sulfonamide (0.5 mmol), arylboronic acid (0.5 mmol) and K2CO3
(1.0 mmol) successively with stirring under reux conditions for
appropriate time (Table 4). Aer completion of the reaction, as
monitored by TLC, the resulting mixture was ltered to separate
the catalyst. Then, the ltrate was cooled to room temperature.
The resulting product was ltered and puried by recrystalliza-
tion using ethyl acetate and n-hexane to afford N-arylated
product. All the products are known compounds and their
physical and spectral data (M.p., IR, NMR) were found to be in
agreement with those reported in the literature.2,5,20–22
References
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N-p-Tolylbenzenesulfonamide (Table 4, entry 1): 1H NMR (90
MHz, CDCl3): d ¼ 2.23 (s, 3H), 6.98–7.84 (m, 10H).
N-(4-Methoxyphenyl)benzenesulfonamide (Table 4, entry 2):
1H NMR (90 MHz, CDCl3): d ¼ 3.70 (s, 3H), 7.07–7.78 (m, 10H).
4-Chloro-N-phenylbenzenesulfonamide (Table 4, entry 3): 1H
NMR (90 MHz, CDCl3): d ¼ 7.07–7.74 (m, 10H).
4-Chloro-N-(4-bromophenyl)benzenesulfonamide (Table 4,
1
entry 4): H NMR (90 MHz, CDCl3): d ¼ 6.90–7.75 (m, 9H).
4-Chloro-N-o-tolylbenzenesulfonamide (Table 4, entry 5): 1H
NMR (90 MHz, CDCl3): d ¼ 2.02 (s, 3H), 6.90–7.72 (m, 9H).
4-Chloro-N-p-tolylbenzenesulfonamide (Table 4, entry 6): 1H
NMR (90 MHz, CDCl3): d ¼ 2.26 (s, 3H), 7.15–7.76 (m, 9H).
4-Chloro-N-(4-methoxyphenyl)benzenesulfonamide (Table 4,
1
entry 7): H NMR (90 MHz, CDCl3): d ¼ 3.76 (s, 3H), 6.55 (br,
1H), 6.70–7.70 (m, 8H).
4-Chloro-N-(2-chlorophenyl)benzenesulfonamide (Table 4,
1
entry 8): H NMR (90 MHz, CDCl3): d ¼ 7.05–7.73 (m, 9H).
N-(4-Bromophenyl)-4-methylbenzenesulfonamide (Table 4,
1
entry 9): H NMR (90 MHz, CDCl3): d ¼ 2.37 (s, 3H), 7.01–7.71
(m, 9H).
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4-Methyl-N-o-tolylbenzenesulfonamide (Table 4, entry 10):
1H NMR (90 MHz, CDCl3): d ¼ 2.01 (s, 3H), 2.35 (s, 3H), 6.86 (br,
1H), 7.15 (d, j ¼ 8.4, 2H), 7.62 (d, j ¼ 7.2, 2H).
N-(2-Chlorophenyl)-4-methylbenzenesulfonamide (Table 4,
entry 11): 1H NMR (90 MHz, CDCl3): d ¼ 2.36 (s, 3H), 7.14–7.69
(m, 9H).
N-(2,6-Dimethylphenyl)-4-methylbenzenesulfonamide (Table 4,
entry 12): 1H NMR (90 MHz, CDCl3): d ¼ 2.03 (s, 6H), 2.41
(s, 3H), 6.05 (br, 1H), 7.01–7.63 (m, 7H).
3 (a) G. Burton, P. Cao, G. Li and R. Rivero, Org. Lett., 2003, 5,
4373; (b) T. Ikawa, T. E. Barder, M. R. Biscoe and
S. L. Buchwald, J. Am. Chem. Soc., 2007, 129, 13001.
N-(4-Chlorophenyl)-4-methylbenzenesulfonamide (Table 4,
entry 13): 1H NMR (90 MHz, CDCl3): d ¼ 2.36 (s, 3H), 7.10–7.63
(m, 9H).
4 (a) P. Toto, J.-C. Gesquiere, N. Cousaert, B. Deprez and
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M. Nasrollahzadeh, J. Mol. Catal. A: Chem., 2014, 383–384,
17.
N-(4-Methoxyphenyl)-4-methylbenzenesulfonamide (Table 4,
1
entry 14): H NMR (90 MHz, CDCl3): d ¼ 2.35 (s, 3H), 3.73 (s,
3H), 6.74–7.56 (m, 9H).
4-Methyl-N-(3-(triuoromethyl)phenyl)benzenesulfonamide
1
(Table 4, entry 15): H NMR (90 MHz, CDCl3): d ¼ 2.32 (s, 3H),
7.29–7.79 (m, 8H), 8.10 (br, 1H).
4-Methyl-N-phenylbenzenesulfonamide (Table 4, entry 16):
1H NMR (90 MHz, CDCl3): d ¼ 2.34 (s, 3H), 7.07–7.74 (m, 10H).
5 H. He and Y.-J. Wu, Tetrahedron Lett., 2003, 44, 3385.
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