a
Org. Chem. 1999, 64, 1338. For recent work, see: (h) Allen, A. E.;
MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260; (i)
Harvey, J. S.; Simonovich, S. P.; Jamison, C. R.; MacMillan, D.
W. C. J. Am. Chem. Soc. 2011, 133, 13782; (j) Bigot, A.;
Williamson, A. E.; Gaunt, M. J. J. Am. Chem. Soc. 2011, 133,
13778; (k) Skucas, E.; MacMillan, D. W. C. J. Am. Chem. Soc.
2012, 134, 9090; (l) Guo, J.; Dong, S.; Zhang, Y.; Kuang, Y.; Liu,
X.; Lin, L.; Feng, X. Angew. Chem. Int. Ed. 2013, 52, 10245.
4. (a) Crowder, J. R.; Glover, E. E.; Grundon, M. F.; Kaempfen, H.
X. J. Chem. Soc. 1963, 4578; (b) Liu, H.; Bernhardsen, M.;
Fiksdahl, A. Tetrahedron 2006, 62, 3564; (c) Marsh, G.; Stenutz,
R.; Bergman, A. Eur. J. Org. Chem. 2003, 2566; (d) Lubinkowski,
J. J.; Knapczyk, J. W.; Calderon, J. L.; Petit, L. R.; McEwen, W.
E. J. Org. Chem. 1975, 40, 3010; (e) Krief, A.; Dumont, W.;
Robert, M. Chem. Commun. 2005, 2167; (f) Petersen, T. B.; Khan,
R.; Olofsson, B. Org. Lett. 2011, 13, 3462.
Reaction conditions: N-arylsulfonamide (0.2 mmol,
1
equiv),
dipenyliodonium triflate (0.24 mmol, 1.2 equiv), CuCl (0.04 mmol, 20
mmol%), K3PO4 (0.4 mmol, 2 equiv), H2O (3 mL).
b Yield of isolated product.
c DCM as the solvent.
Further exploration of the scope of the reaction was conducted
with various substituted N-arylsulfonamides. With 2a, substituted
N-arylsulfonamides with flouro-, chloro-, bromo-groups on the
aromatic ring reacted smoothly and formed the corresponding
products (Table 3, entries 2-4), among which chloro-group gave
a relatively low yield (Table 3, entry 3). N-arylsulfonamides
containing electron-donating substituents (4-MeO, 2-Me) also
gave the excellent yields (Table 3, entries 6, 7), whereas the -
NMe2 afforded desired product in moderate yield (Table 3, entry
5). And the electron-withdrawing nitro-group proved to be
suitable substrate (Table 3, entry 8). Additionally, N-
butylsulfonamide was also viable substrate, providing desired
product in 62% yield and 90% yield in DCM (Table 3, entry 9).
However, N-cyclohexylsulfonamide with steric hindrance gave
<5% desired product in water and 20% yield in DCM (Table 3,
entry 10). Furthermore, substituted N-arylsulfonamides on the
sulfonamide ring were investigated, use of 1k as substrate gave
the corresponding product in 23% yield and 92% yield in DCM
(Table 3, entry 11). Meanwhile, 1l could also give desired
product with excellent yield (Table 3, entry 12).
5. (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am.
Chem. Soc. 2005, 127, 7330; (b) Deprez, N. R.; Kalyani, D.;
Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972; (c)
Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc.
2008, 130, 8172; (d) Deprez, N. R.; Sanford, M. S. J. Am. Chem.
Soc. 2009, 131, 11234; (e) Phipps, R. J.; Gaunt, M. J. Science
2009, 323, 1593; (f) Xiao, B.; Fu, Y.; Xu, J.; Gong, J. J.; Dai, J.
Y.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468; (g) Ciana, C. L.;
Phipps, R. J.; Brandt, J. R.; Meyer, F. M.; Gaunt, M. J. Angew.
Chem. 2011, 123, 478; Angew. Chem. Int. Ed. 2011, 50, 458; (h)
Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt,
M. J. Angew. Chem. 2011, 123, 483; Angew. Chem. Int. Ed. 2011,
50, 463; (i) Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.;
Guant, M. J. J. Am. Chem. Soc. 2012, 134, 10773; (j) Suero, M.
G.; Bayle, E. D.; Collins, B. S. L.; Guant, M. J. J. Am. Chem. Soc.
2013, 135, 5332; (k) Guo, F. L.; Han, J. W.; Mao, S.; Li, J.; Geng,
X.; Yu, J. J.; Wang, L. M. RSC Adv 2013, 3, 6267.
3. Conclusion
6. (a) Kitamura, T.; Yamane, M.; Inoue, K.; Todaka, M.; Fukatsu,
N.; Meng, Z.; Fujiwara, Y. J. Am. Chem. Soc. 1999, 121, 11674;
(b) Xue, J.; Huang, X. Synth. Commun. 2007, 37, 2179.
In summary, we have developed a new protocol for the
synthesis of N’N-diarylsulfonamides using diaryliodonium salts
as the electrophilic coupling partners in the presence of a copper
catalyst. The starting material N-arylsulfonamides can be easily
prepared from corresponding arylamines and sulfonyl chlorides.
The reaction is simple to perform and takes place in water under
mild conditions, giving the products in moderate to excellent
yields.
7. (a) Supuran, C. T.; Casini, A.; Scozzafava, A. Med. Res. Rev.
2003, 5, 535; (b) Scozzafava, A.; Owa, T.; Mastrolorenzo, A.;
Supuran, C. T. Curr. Med. Chem. 2003, 10, 925.
8. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.;
Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.;
Anderson, P. S.; Lotti, V. J.; Cerino, D. J.; Chen, T.B.; Kling, P.
J.; Kunkerl, K. A.; Springer, J. P.; Hirshfield, J. J. Med. Chem.
1998, 31, 2235.
9. (a) Wright, S. W.; Hallstrom, K. N. J. Org. Chem. 2006, 71, 1080;
(b) Katritzky, A. R.; Abdel-Fattah, A. A. A.; Vakulenko, A. V.;
Tao, H. J. Org. Chem. 2005, 70, 9191; (c) Caddick, S.; Wilden, J.
D.; Judd, D. B. J. Am. Chem. Soc. 2004, 126, 1024; (d) Pandya,
R.; Murashima, T.; Tedeschi, L.; Barrett, A. G. M. J. Org. Chem.
2003, 68, 8274; (e) Lee, J.; Louie, Y. Q.; Walsh, D. P.; Chang, Y.
T. J. Comb. Chem. 2003, 5, 330; (f) Frost, C. G.; Hartley, J. P.;
Griffin, D. Synlett 2002, 1928; (g) Abid, M.; Teixeira, L.; Török,
B. Tetrahedron Lett. 2007, 48, 4047; (h) Marcotullio, M. C.;
Campagna, V.; Sternativo, S.; Costantino, F.; Curini, M. Synthesis
2006, 2760; (i) Hamid, M. H. S. A.; Allen, C. L.; Lamb, G. W.;
Maxwell, A. C.; Maytum, H. C.; Watson, A. J. A.; Williams, J. M.
J. Am. Chem. Soc. 2009, 131, 1766; (k) Bhuyan, R.; Nicholas, K.
M. Org. Lett. 2007, 9, 3957.
Acknowledgments
The work was supported by the National Nature Science
Foundation of China (NSFC, 21272069), the Fundamental
Research Funds for the Central Universities and Key Laboratory
of Organofluorine Chemistry, Shanghai Institute of Organic
Chemistry, Chinese Academy of Sciences.
References and notes
1. (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523; (b)
Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299; (c)
Merritt, E. A.; Olofsson, B. Angew. Chem. Int. Ed. 2009, 48, 9052;
(d) Silva, L. F.; Olofsson, B. Nat. Prod. Rep. 2011, 28, 1722; (e)
Yusubov, M. S.; Zhdankin, V. V. Curr. Org. Synth. 2012, 9, 247.
2. (a) Kang, S. K.; Lee, S. H.; Lee, D. Synlett 2000, 1022; (b)
Beletskaya, I. P.; Davydov, D. V.; Gorovoy, M. S. Tetrahedron
Lett. 2002, 43, 6221; (c) Zhou, T.; Chen, Z. C. Synth. Commun.
2002, 32, 903; (d) Wang, F. Y.; Chen, Z. C.; Zheng, Q. G. J.
Chem. Res. 2004, 206; (e) Niu, H. Y.; Xia, C.; Qu, G. R.; Zhang,
Q.; Jiang, Y.; Mao, R. Z.; Li, D. Y.; Guo, H. M. Org. Biomol.
Chem. 2011, 9, 5039; (f) Vaddula, B.; Leazer, J.; Varma, R. S.
Adv. Synth. Catal. 2012, 354, 986; (g) Guo, F. L.; Wang, L. M.;
Wang, P. Q.; Yu, J. J.; Han, J. W. Asian J. Org. Chem. 2012, 1,
218-221; (h) Mao, S.; Guo, F. L.; Li, J.; Geng, X.; Han, J. W.;
Wang, L. M.; Synlett 2013, 24, 1959.
3. (a) Beringer, F. M.; Galton, S. A. J. Org. Chem. 1963, 28, 3417;
(b) Hampton, K. G.; Harris, T. M.; Hauser, C. R. J. Org. Chem.
1964, 29, 3511; (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991,
56, 5764; (d) Gao, P.; Portoghese, P. S. J. Org. Chem. 1995, 60,
2276; (e) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38,
5061; (f) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H.
Org. Lett. 1999, 1, 673; (g) Oh, C. H.; Kim, J. S.; Jung, H. H. J.
10. (a) Andersen, K. K. In Comprehensive Organic Chemistry; Jones,
D. N.; Pregamaon Press: Oxford, 1979; Vol. 3; (b) Graham, S. L.;
Scholz, T. H. Synthesis 1986, 852; (b) Chan, W. Y.; Berthelette,
C. Tetrahedron Lett. 2002, 43, 4537; (c) Park, K. K.; Lee, J. J.;
Ryu, J. Tetrahedron 2003, 59, 7651; (d) Deng, X.; Mani, N. S.
Green Chem. 2006, 8, 835; (e) Shaabani, A.; Soleimani, E.;
Rezayan, A. H. Tetrahedron Lett. 2007, 48, 2185; (f) Meshram, G.
A.; Patil, V. D. Tetrahedron Lett. 2009, 50, 1117; (g) Jafarpour,
M.; Rezaeifard, A.; Aliabadi, M. Appl. Catal. A. 2009, 358, 49; (h)
Reddy, M. B. M.; Pasha, M. A. Phosphorus, Sulfur, and Silicon
2011, 186, 1867; (i) Zarchi, M. A. K.; Aslani, M. J. Appl. Poly.
Sci. 2012, 124, 3456-3462.
11. (a) Ullmann, F.; Sponagel, P. Ber. Dtsch. Chem. Ges. 1905, 2211;
(b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 1691; (c) Muci, A.
R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131; (d)
Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534; (e) Zhang, M.;
Zhang, A. Synthesis 2012, 44, 1; (f) Surry, D. S.; Buchwald, S. L.
Chem. Sci. 2011, 2, 27; (g) Sadig, J. E. R.; Willis, M. C. Synthesis
2011, 1, 1; (h) Surry, D. S.; Buchwald, S. L. Angew. Chem. Int.
Ed. 2008, 47, 6338; (i) Hartwig, J. F. Nature 2008, 455, 314.