Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of potassium 2-pyridyl trifluoroborate with aryl (heteroaryl) halides

Tetrahedron

Volumn 68, Issue 5, 2012, Pages 1351-1358

  Ren, Wei ^a,b   Li, Jingya ^b   Zou, Dapeng ^a,b   Wu, Yangjie ^a   Wu, Yusheng ^b,c  

^a ZHENGZHOU UNIVERSITY   (China)

^b Tetranov Biopharm   (China)

^c Tetranov International   (United States)

Author keywords

Aryl (heteroaryl) halides; Palladium catalyzed; Potassium 2 pyridyl trifluoroborate; Suzuki Miyaura cross coupling reaction

Indexed keywords

ALCOHOL; FLUORINE DERIVATIVE; HALIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM; PYRIDINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SUZUKI REACTION;

EID: 84855605030     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.12.036     Document Type: Article

References (33)

1. L. Ackermann, and H.K. Potukuchi Synlett 2009 2852
2. K.M. Meyers, N. Kim, J.L. Mendez-Andino, X.E. Hu, R.N. Mumin, S.R. Klopfenstein, J.A. Wos, M.C. Mitchell, J.L. Paris, D.C. Ackley, J.K. Holbert, S.W. Mittelstadt, and O. Reizes Bioorg. Med. Chem. Lett. 17 2007 814
3. L. Ackermann, H.K. Potukuchi, A.R. Kapdi, and C. Schulzke Chem. - Eur. J. 16 2010 3300
4. S. Napier, S.M. Marcuccio, H. Tye, and M. Whittaker Tetrahedron Lett. 49 2008 6314
5. B.M. Coleridge, C.S. Bello, D.H. Ellenberger, and A. Leitner Tetrahedron Lett. 51 2010 357
6. K. Deshayes, R.D. Broene, I. Chao, C.B. Knobler, and F. Diederich J. Org. Chem. 56 1991 6787
7. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
8. A. Suzuki J. Organomet. Chem. 576 1999 147
9. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633
10. S. Darses, and J.P. Genet Chem. Rev. 108 2008 288
11. R.J. Lindup, T.B. Marder, R.N. Perutz, and A.C. Whitwood Chem. Commun. 2007 3664
12. D.W. Old, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 9722
13. J.P. Wolfe, R.A. Singer, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9550
14. R.B. Bedford, and C.S.J. Cazin Chem. Commun. 2001 1540
15. J.H. Kirchoff, C. Dai, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 1945
16. G.A. Grasa, M.S. Viciu, J. Huang, C. Zhang, M.L. Trudell, and S.P. Nolan Organometallics 21 2002 2866
17. M. Feuerstein, F. Berthiol, H. Doucet, and M. Santinelli Synlett 2002 1807
18. G.A. Molander, and T. Fumagalli J. Org. Chem. 71 2006 5743
19. K.L. Billingsley, and S.L. Buchwald Angew. Chem., Int. Ed. 47 2008 4695
20. For examples, of Suzuki-Miyaura reactions of 2-pyridylboronic acids, see: S.D. Mandolesi, S.E. Vaillard, J.C. Podesta, and R.A. Rossi Organometallics 21 2002 4886
21. A. Bouillon, J.C. Lancelot, J. S. de O. Santos, V. Collot, P.R. Bovy, and S. Rault Tetrahedron 59 2003 10043
22. T. Shinozuka, K. Shimada, S. Matsui, T. Yamane, M. Ama, T. Fukuda, M. Taki, Y. Takeda, E. Otsuka, M. Yamato, and S. Naito Bioorg. Med. Chem. 14 2006 6807
23. J.Z. Deng, D.V. Paone, A.T. Ginnetti, H. Kurihara, S.D. Dreher, S.A. Weissman, S.R. Stauffer, and C.S. Burgey Org. Lett. 11 2009 345
24. D.X. Yang, S.L. Colletti, K. Wu, M.Y. Song, G.Y. Li, and H.C. Shen Org. Lett. 11 2009 381
25. P.B. Hodgson, and F.H. Salingue Tetrahedron Lett. 45 2004 685
26. P. Gros, A. Doudouh, and Y. Fort Tetrahedron Lett. 45 2004 6239
27. Y. Yamamoto, M. Takizawa, X.Q. Yu, and N. Miyaura Angew. Chem., Int. Ed. 47 2008 928
28. O.M. Knapp, E.P. Gillis, and M.D. Burke J. Am. Chem. Soc. 131 2009 6961
29. G.A. Molander, B. Canturk, and L.E. Kennedy J. Org. Chem. 74 2009 973
30. S. Darses, and J.P. Genet Eur. J. Org. Chem. 22 2003 4313
31. G.A. Molander, and N. Ellis Acc. Chem. Res. 40 2007 275
32. H.A. Stefani, R. Cella, and S.A. Vieira Tetrahedron 63 2007 3623
33. G.A. Molander, and B. Biolatto J. Org. Chem. 68 2003 4302