Efficient palladium(II)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives

Tetrahedron

Volumn 67, Issue 31, 2011, Pages 5550-5555

  Li, Ziyuan ^a   Wang, Yiyun ^a   Huang, Yue ^a   Tang, Changhua ^a   Xu, Jinyi ^a   Wu, Xiaoming ^a   Yao, Hequan ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

C H bond activation; Homocoupling; Oxazole; Palladium(II) catalyzed; Thiazole

Indexed keywords

OXAZOLE 4 CARBOXYLIC DERIVATIVE; OXAZOLE DERIVATIVE; PALLADIUM; THIAZOLE 4 CARBOXYLIC DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; HOMOCOUPLING REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 79959724121     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.123     Document Type: Article

References (35)

1. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
2. R.F. Heck B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford 833
3. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
4. T.Y. Luh, M.K. Leung, and K.T. Wong Chem. Rev. 100 2000 3187
5. T. Hiyama J. Organomet. Chem. 653 2002 58
6. E.I. Negishi, Q. Hu, Z. Huang, M. Qian, and G. Wang Aldrichimica Acta 38 2005 71
7. B.M. Trost, and M.L. Crawley Chem. Rev. 103 2003 2921
8. K.C. Nicolaou, P.G. Bulger, and D. Sarlah Angew. Chem., Int. Ed. 44 2005 4442
9. D.S. Surry, and S.L. Buchwald Angew. Chem., Int. Ed. 47 2008 6338
10. J.F. Hartwig Nature 455 2008 314
11. S.E. Denmark, and C.S. Regens Acc. Chem. Res. 41 2008 1486
12. L.M. Xu, B.J. Li, Z. Yang, and Z.J. Shi Chem. Soc. Rev. 39 2010 712
13. R.H. Crabtree Chem. Rev. 85 1985 245
14. A.E. Shilov, and G.B. Shulpin Chem. Rev. 97 1997 2879
15. S.S. Stahl, J.A. Labinger, and J.E. Bercaw Angew. Chem., Int. Ed. 37 1998 2180
16. R.G. Bergman Nature 446 2007 391
17. M. Brookhart, M.L.H. Green, and G. Parkin Proc. Natl. Acad. Sci. U.S.A. 104 2007 6908
18. D.R. Stuart, and K. Fagnou Science 316 2007 1172
19. X. Chen, K.M. Engle, D.H. Wang, and J.Q. Yu Angew. Chem., Int. Ed. 49 2009 5094
20. R.L. Rice, J.M. Rusnak, F. Yokokawa, S. Yokokawa, D. Messner, A.L. Boynton, P. Wipf, and J.S. Lazo Biochemistry 36 1997 15965
21. Y. Huang, L. Ni, H. Gan, Y. He, J. Xu, X. Wu, and H. Yao Tetrahedron 67 2011 2066
22. D.H. Kim, B.L. Lee, H. Moon, H.M. Kang, E.J. Jeong, J.I. Park, K.M. Han, S. Lee, B.W. Yoo, B.W. Koo, J.Y. Kim, W.H. Lee, K. Cho, H.A. Becerril, and Z. Bao J. Am. Chem. Soc. 131 2009 6124
23. A. Wakamiya, T. Taniguchi, and S. Yamaguchi Angew. Chem., Int. Ed. 45 2006 3170
24. F.A. Romero, W. Du, I. Hwang, T.J. Rayl, F.S. Kimball, D. Leung, H.S. Hoover, R.L. Apodaca, J.G. Breitenbucher, B.F. Cravatt, and D.L. Boger J. Med. Chem. 50 2007 1058
25. G.L. Turner, J.A. Morris, and M.F. Greaney Angew. Chem., Int. Ed. 46 2007 7996
26. J. Hammerle, M. Spina, M. Schnurch, M.D. Mihovilovic, and P. Stanetty Synthesis 2008 3099
27. J. Hammerle, M. Schnurch, and P. Stanetty Synlett 2007 2975
28. P. Stanetty, M. Schnurch, and M.D. Mihovilovic J. Org. Chem. 71 2006 3754
29. T. Kauffmann Angew. Chem., Int. Ed. Engl. 13 1974 291
30. J. Kagan, and K. Arora Heterocycles 20 1983 1937
31. K. Masui, H. Ikegami, and A. Mori J. Am. Chem. Soc. 126 2004 5074
32. J.B. Xia, X.Q. Wang, and S.L. You J. Org. Chem. 74 2009 456
33. Z. Liang, J. Zhao, and Y. Zhang J. Org. Chem. 75 2010 170
34. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, and J. You J. Am. Chem. Soc. 132 2010 1822
35. W. Han, P. Mayer, and A.R. Ofial Angew. Chem., Int. Ed. 50 2011 2178