Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions

Tetrahedron Letters

Volumn 53, Issue 1, 2012, Pages 7-10

  Wang, Xiang ^a   Guram, Anil ^b   Ronk, Michael ^b   Milne, Jacqueline E ^b   Tedrow, Jason S ^b   Faul, Margaret M ^b  

^a Process Research and Development Gilead Sciences   (United States)

^b AMGEN INC   (United States)

Author keywords

Copper catalysis; N Arylation; Sulfonamide coupling

Indexed keywords

BROMIDE; COPPER; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONAMIDE;

ARTICLE; ARYLATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ROOM TEMPERATURE;

EID: 82955198385     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.113     Document Type: Article

References (23)

1. For a list of sulfonamide-containing drugs, see: D.A. Smith, and R.M. Jones Curr. Opin. Drug Discov. Devel. 2008 72 79
2. A. Scozzafava, T. Owa, A. Mastrolorenzo, and C.T. Supuran Curr. Med. Chem. 10 2003 925 953
3. P.L. Skipper, M.Y. Kim, H.L. Sun, G.N. Wogan, and S.R. Tannenbaum Carcinogenesis 31 2009 50 58
4. For recent work on Pd-catalyzed sulfonamide coupling, see: T. Ikawa, T.E. Barder, M.R. Biscoe, and S.L. Buchwald J. Am. Chem. Soc. 129 2007 13001 13007
5. B.R. Rosen, J.C. Ruble, T.J. Beauchamp, and A. Navarro Org. Lett. 13 2011 2564 2567
6. S. Shekhar, T.B. Dunn, B.J. Kotecki, D.K. Montavon, and S.C. Cullen J. Org. Chem. 76 2011 4552 4563
7. D. Steinhuebel, M. Palucki, D. Askin, and U. Dolling Tetrahedron Lett. 45 2004 3305 3307
8. G. Burton, P. Cao, G. Li, and R. Rivero Org. Lett. 5 2003 4373 4376
9. J.D. Hicks, A.M. Hyde, A.M. Cuezva, and S.L. Buchwald J. Am. Chem. Soc. 131 2009 16720 16734
10. P. Anjanappa, D. Mullick, K. Selvakumar, and M. Sivakumar Tetrahedron Lett. 49 2008 4585 4587
11. L. Alcaraz, C. Bennion, J. Morris, P. Meghani, and S.M. Thom Org. Lett. 6 2004 2705 2708
12. T. Ikawa, T.E. Barder, M.R. Biscoe, and S.L. Buchwald J. Am. Chem. Soc. 129 2007 13001 13007
13. For recent work on Cu-catalyzed sulfonamide and amide coupling with aryl halides, see: A. Klapars, J.C. Antilla, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 7727 7729
14. H. He, and Y.J. Wu Tetrahedron Lett. 44 2003 3385 3386
15. J. Baffoe, M.Y. Hoe, and B.B. Toure Org. Lett. 12 2010 1532 1535
16. W. Deng, L. Liu, C. Zhang, M. Liu, and Q.X. Guo Tetrahedron Lett. 46 2005 7295 7298
17. X.J. Han Tetrahedron Lett. 51 2010 360 362
18. D. Audisio, S. Messaoudi, J.F. Peyrat, J.D. Brion, and M. Alami J. Org. Chem. 76 2011 4995 5005
19. W. Deng, L. Liu, C. Zhang, M. Liu, and Q.-X. Guo Tetrahedron Lett. 46 2005 7295 7298
20. For the coupling of aryl boronic acids with sulfonamides using a stoichiometric amount of oxidant, see: D.M.T. Chan, K.L. Monaco, R.-P. Wang, and M.P. Winters Tetrahedron Lett. 39 1998 2933 2936
21. P.Y.S. Lam, G. Vincent, C.G. Clark, S. Deudon, and P.K. Jadhav Tetrahedron Lett. 42 2001 3415 3418
22. In comparison, CuI/amino acid system operated at 140 °C/48 h, see Ref. 4d. For use of amino acids as ligands in Cu-catalyzed cross coupling reactions, see: D. Ma, Y. Zhang, J. Yao, S. Wu, and F. Tao J. Am. Chem. Soc. 120 1998 12459 12467
23. For SNAr reaction of sulfonamides with 2-Cl pyridines bearing additional electron withdrawing groups, see: G.M. Coppola, and G.E. Hardtmann J. Heterocycl. Chem. 16 1979 1361 1363