Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones

Journal of Molecular Catalysis A: Chemical

Volumn 383-384, Issue , 2014, Pages 94-100

  Cao, Xiangxiang ^a   Bai, Yang ^a   Xie, Yanjun ^a   Deng, Guo Jun ^a,b  

^a XIANGTAN UNIVERSITY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

Aromatization; Arylation; Cyclohexanones; Dehydrogenation; Sulfonamides

Indexed keywords

ARYLATIONS; CYCLOHEXANONES; PALLADIUM-CATALYZED ARYLATION; SULFONAMIDES;

AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; DEHYDROGENATION; SULFUR COMPOUNDS;

AMIDES;

EID: 84890855388     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2013.11.023     Document Type: Article

References (82)

1. D.A. Smith, and R.M. Jones Curr. Opin. Drug Discov. Dev. 11 2008 72 79
2. A. Scozzafava, T. Owa, A. Mastrolorenzo, and C.T. Supuran Curr. Med. Chem. 10 2003 925 953
3. J.D. Wilden J. Chem. Res. 34 2010 541 547
4. M.A. Navia Science 288 2000 2132 2133
5. S.K. Mohamed Afinidad 57 2000 451 456
6. N.S. Reddy, M.R. Mallireddigari, S. Cosenza, K. Gumireddy, S.C. Bell, E.P. Reddy, and M.V.R. Reddy Bioorg. Med. Chem. Lett. 14 2004 4093 4097
7. M. Banerjee, A. Poddar, G. Mitra, A. Surolia, T. Owa, and B. Bhattacharyya J. Med. Chem. 48 2005 547 555
8. A. Natarajan, Y. Guo, F. Harbinski, Y.H. Fan, H. Chen, L. Luus, J. Diercks, H. Aktas, M. Chorev, and J.A. Halperin J. Med. Chem. 47 2004 4979 4982
9. C. Monyalbetti, and V. Falque Tetrahedron 61 2005 10827 10852
10. E. Valeur, and M. Bradley Chem. Soc. Rev. 38 2009 606 631
11. A. El-Faham, and F. Albericio Chem. Rev. 111 2011 6557 6602
12. C.G. Frost, J.P. Hartley, and D. Griffin Synlett 11 2002 1928 1930
13. J.W. Lee, Y.Q. Louie, D.P. Walsh, and Y.T. Chang J. Comb. Chem. 5 2003 330 335
14. R. Pandya, T. Murashira, L. Tedeschi, and A.G.M. Barrett J. Org. Chem. 68 2003 8274 8276
15. S. Caddick, J.D. Wilden, and D.B. Judd J. Am. Chem. Soc. 126 2004 1024 1205
16. A.R. Katritzky, A. Abdel-Fattah, A.V. Vakulenko, and H. Tao J. Org. Chem. 70 2005 9191 9197
17. S.W. Wright, and K.N. Hallstrom J. Org. Chem. 71 2006 1080 1084
18. J. Wilden, L. Geldeard, C. Lee, D. Judd, and S. Caddick Chem. Commun. 10 2007 1074 1076
19. K. Bahrami, M. Khodaei, and M. Soheilizad J. Org. Chem. 74 2009 9287 9291
20. C. Pan, J. Chang, H. Wu, J. Ding, and M. Liu Syn. Commun. 39 2009 2082 2092
21. S. Lavy, J. Miller, M. Pazicky, A. Rodrigues, C. Jaekel, D. Serra, N. Vinokurov, M. Limbach, and F. Rominger Adv. Synth. Catal. 352 2010 2993 3000
22. K.K. Andersen D.N. Jones, Comprehensive Organic Chemistry vol. 3 1979 Pergamon Oxford 331 340
23. J. Baffoe, M. Hoe, and B. Touré Org. Lett. 12 2010 1532 1535
24. A. Gonzalez-Gomez, G. Dominguez, and J. Perez-Castells Eur. J. Org. Chem. 2009 5057 5062
25. M. Haemata, P. Zheng, C. Huang, M. Gomes, W. Ying, K. Ranyanil, G. Balan, and N. Calkins J. Org. Chem. 72 2007 683 685
26. A. Kamal, J. Reddy, E. Bharathi, and D. Dastagiri Tetrahedron Lett. 49 2008 348 353
27. X. Deng, and N. Mani Green Chem. 8 2006 835 838
28. R. Sridhar, B. Srinivas, V. Kumar, M. Narender, and K. Rao Adv. Synth. Catal. 349 2007 1873 1876
29. J.P. Wolfe, S. Wagaw, J.F. Marcoux, and S.L. Buchwald Acc. Chem. Res. 31 1998 805 818
30. J.F. Hartwig Acc. Chem. Res. 31 1998 852 860
31. J.F. Hartwig Acc. Chem. Res. 41 2008 1534 1544
32. D.S. Surry, and S.L. Buchwald Angew. Chem. Int. Ed. 47 2008 6338 6361
33. I.P. Beletskaya, and A.V. Cheprakov Coord. Chem. Rev. 248 2004 2337 2364
34. G. Evano, N. Blanchard, and M. Toumi Chem. Rev. 108 2008 3054 3131
35. F. Monnier, and M. Taillefer Angew. Chem. Int. Ed. 48 2009 6954 6971
36. D.M.T. Chan, K.L. Monaco, R.P. Wang, and M.P. Winters Tetrahedron Lett. 39 1998 2933 2936
37. P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, M.P. Winters, D.M.T. Chan, and A. Combs Tetrahedron Lett. 39 1998 2941 2944
38. S.V. Ley, and A.W. Thomas Angew. Chem. Int. Ed. 42 2003 5400 5449
39. K.I. Fujita, and R. Yamaguchi Synlett 4 2005 560 571
40. G. Guillena, D. Ramón, and M. Yus Angew. Chem. Int. Ed. 46 2007 2358 2364
41. M. Hamid, P. Slatford, and J.M.J. Williams Adv. Synth. Catal. 349 2007 1555 1575
42. T.D. Nixon, M.K. Whittlesey, and J.M.J. Williams Dalton Trans. 5 2009 753 762
43. G. Guillena, D.J. Ramón, and M. Yus Chem. Rev. 110 2010 1611 1641
44. A. Watson, and J.M.J. Williams Science 329 2010 635 636
45. R. Grigg, T.R.B. Mitchell, S. Sutthivaiyakit, and N. Tongpenyai J. Chem. Soc. Chem. Commun. 1981 611 612
46. Y. Watanable, Y. Tsuji, and Y. Ohsugi Tetrahedron Lett. 22 1981 2667 2670
47. Y. Watanable, Y. Tsuji, H. Ige, Y. Ohsugi, and T. Ohta J. Org. Chem. 49 1984 3359 3363
48. X. Cui, F. Shi, Y.Q. Deng, M. Tse, M. Beller, D. Gourde's, and K. Thurow Adv. Synth. Catal. 351 2009 2949 2958
49. M. Zhu, K. Fujita, and R. Yamaguchi Org. Lett. 12 2010 1336 1339
50. X. Yu, C. Liu, L. Jiang, and Q. Xu Org. Lett. 13 2011 6184 6187
51. X. Cui, Y. Zhang, F. Shi, and Y.Q. Deng Chem. Eur. J. 17 2011 1021 1028
52. R. Cano, D. Ramon, and M. Yus J. Org. Chem. 76 2011 5547 5557
53. C. Liu, S. Liao, Q. Li, S. Feng, Q. Sun, X. Yu, and Q. Xu J. Org. Chem. 76 2011 5759 5773
54. C. Feng, Y. Liu, S.M. Peng, Q. Shuai, G.J. Deng, and C.J. Li Org. Lett. 12 2010 4888 4891
55. Y. Liu, W. Chen, C. Feng, and G.J. Deng Chem. Asian J. 6 2011 1142 1146
56. F. Xiao, Y. Liu, C. Tang, and G.J. Deng Org. Lett. 14 2012 984 987
57. M. Wu, X. Hu, J. Liu, Y. Liao, and G.J. Deng Org. Lett. 14 2012 2722 2725
58. E.C. Horning, and M.G. Horning J. Am. Chem. Soc. 69 1947 1359 1366
59. P. Bamfield, and P.F. Gordon Chem. Soc. Rev. 13 1984 441 488
60. T.T. Wenzel J. Chem. Soc. Chem. Commun. 1989 932 933
61. J. Muzart J. Eur. J. Org. Chem. 2010 3779 3790
62. P. Horrillo-Martinez, M.A. Virolleaud, and C. Jaekel ChemCatChem 2 2010 175 181
63. Y. Izawa, D. Pun, and S.S. Stahl Science 333 2011 209 213
64. T. Diao, and S.S. Stahl J. Am. Chem. Soc. 133 2011 14566 14569
65. T. Diao, T. Wadzinski, and S.S. Stahl Chem. Sci. 3 2012 887 891
66. S. Girard, X. Hu, T. Knauber, F. Zhou, M. Simon, G.J. Deng, and C.J. Li Org. Lett. 14 2012 5606 5609
67. M. Simon, S.A. Girard, and C.J. Li Angew. Chem. Int. Ed. 51 2012 7537 7540
68. F. Xiao, Y. Liao, M. Wu, and G.J. Deng Green Chem. 14 2012 3277 3280
69. A. Hajra, Y. Wei, and N. Yoshika Org. Lett. 14 2012 5488 5491
70. M. Barros, S. Dey, C. Maycock, and P. Rodrigues Chem. Commun. 48 2012 10901 10903
71. M. Sutter, N. Sotto, Y. Raoul, E. Métay, and M. Lemaire Green Chem. 15 2013 347 352
72. M. Sutter, R. Lafon, Y. Raoul, E. Métay, and M. Lemaire Eur. J. Org. Chem. 26 2013 5902 5916
73. Y. Xie, S. Liu, Y. Liu, Y. Wen, and G.J. Deng Org. Lett. 14 2012 1692 1695
74. T. Ishikawa, E. Uedo, R. Tani, and S. Saito J. Org. Chem. 66 2001 186 191
75. H. Ge, M.J. Niphakis, and G.I. Georg J. Am. Chem. Soc. 130 2008 3708 3709
76. J.J. Neumann, S. Rakshit, T. Dröge, S. Würtz, and F. Glorius Chem. Eur. J. 17 2011 7298 7303
77. S.S. Stahl, J.L. Thorman, R.C. Nelson, and M.A. Kozee J. Am. Chem. Soc. 123 2001 7188 7189
78. J.A. Mueller, C.P. Goller, and M.S. Sigman J. Am. Chem. Soc. 126 2004 9724 9734
79. B.A. Steinhoff, I.A. Guzei, and S.S. Stahl J. Am. Chem. Soc. 126 2004 11268 11278
80. M.M. Konnick, I.A. Guzei, and S.S. Stahl J. Am. Chem. Soc. 126 2004 10212 10213
81. J. Muzart Chem. Asian J. 1 2006 508 1515
82. M.M. Konnick, and S.S. Stahl J. Am. Chem. Soc. 130 2008 5753 5762