A general and special catalyst for suzuki-miyaura coupling processes

Angewandte Chemie - International Edition

Volumn 49, Issue 34, 2010, Pages 5879-5883

  Tang, Wenjun ^a   Capacci, Andrew G ^a   Wei, Xudong ^a   Li, Wenjie ^a   White, Andre ^a   Patel, Nitinchandra D ^a   Savoie, Jolaine ^a   Gao, Joe J ^a   Rodriguez, Sonia ^a   Qu, Bo ^a   Haddad, Nizar ^a   Lu, Bruce Z ^a   Krishnamurthy, Dhileepkumar ^a   Yee, Nathan K ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

Cross coupling; Monophosphanes; Palladium; Phosphorus ligands; Suzuki Miyaura coupling

Indexed keywords

ARYLBORONIC ACIDS; COUPLING REACTION; CROSS-COUPLING; CROSS-COUPLINGS; EXCELLENT PERFORMANCE; PHOSPHORUS LIGANDS; SUZUKI-MIYAURA COUPLING; SUZUKI-MIYAURA COUPLING PROCESS; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

LIGANDS; PALLADIUM; PHOSPHORUS;

CHEMICAL REACTIONS;

BORONIC ACID DERIVATIVE; LIGAND; PALLADIUM; PHOSPHORUS;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; X RAY CRYSTALLOGRAPHY;

BORONIC ACIDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; LIGANDS; MOLECULAR CONFORMATION; PALLADIUM; PHOSPHORUS;

EID: 77955582938     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002404     Document Type: Article

References (48)

1. N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 1979, 36, 343.
2. For selected reviews, see: a) A. Suzuki, J. Organomet. Chem. 1999, 576, 147;
3. b) N. Miyaura, Top. Curr. Chem. 2002, 219, 11;
4. c)N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
5. d) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
6. e) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633;
7. f) A. F. Littke, G.C. Fu, Angew. Chem. 2002, 114, 4350;
8. Angew. Chem. Int. Ed. 2002, 41, 4176;
9. g) F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 2419;
10. h) U. Christmann, R. Vilar, Angew. Chem. 2005, 117, 370;
11. Angew. Chem. Int. Ed. 2005, 44, 366;
12. F. Alonso, I.P. Beletskaya, M. Yus, Tetrahedron 2008, 64, 3047;
13. j) Metal-Catalyzed CrossCoupling Reactions, Vol. 2 (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
14. k) Modern Arylation Methods (Ed.: L. Ackermann), Wiley-VCH, Weinheim, 2009.
15. a) M. Miura, Angew. Chem 2004, 116, 2251;
16. Angew. Chem. Int. Ed. 2004, 43, 2201;
17. b) R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461.
18. a) W. Shen, Tetrahedron Lett. 1997, 38, 5575;
19. b) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586;
20. Angew. Chem. Int. Ed. 1998, 37, 3387;
21. c) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020;
22. d) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315;
23. Angew. Chem. Int. Ed. 2000, 39, 4153;
24. e) J. P. Stambuli, R. Kuwano, J. F. Hartwig, Angew. Chem. 2002, 114, 4940;
25. Angew. Chem. Int. Ed 2002, 41, 4746;
26. f) C. A. Fleckenstein, H. Plenio, Chem. Eur. J. 2007, 13, 2701;
27. g) C. A. Fleckenstein, H. Plenio, J. Org. Chem. 2008, 73, 3236.
28. a) N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553;
29. b) A. S. Guram, A. O. King, J. G. Allen, X. Wang, L. B. Schenkel, J. Chan, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, P. J. Reider, Org. Lett. 2006, 8, 1787;
30. c) T. Hoshi, T. Nakazawa, I. Saitoh, A. Mori, T. Suzuki, J. Sakai, H. Hagiwara, Org. Lett. 2008, 10, 2063;
31. T. Hoshi, I. Saitoh, T. Nakazawa, T. Suzuki, J.-i, Sakai, H. Hagiwara, J. Org. Chem. 2009, 74, 4013.
32. a) J. P. Wolfe, R. A. Singer, B. H. Yang, J. Am. Chem. Soc. 1999, 121, 9550;
33. b) J. Yin, S. L. Buchwald, J. Am. Chem. Soc 2000, 122, 12051;
34. c) J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162;
35. d) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907;
36. Angew. Chem. Int. Ed 2004, 43, 1871;
37. e) T. E. Barder, S.D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685;
38. f) K. L. Billingsley, K. W. Anderson, S. L. Buchwald, Angew. Chem. 2006, 118, 3564;
39. Angew. Chem. Int. Ed. 2006, 45, 3484;
40. g) K. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358;
41. h) C. M. So, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 8179;
42. Angew. Chem Int. Ed. 2008, 47, 8059;
43. B. Bhayana, B. P. Fors, S. L. Buchwald, Org. Lett. 2009, 11, 3954.
44. a) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W.A. Herrmann, Angew. Chem. 2002, 114, 1421;
45. Angew. Chem. Int. Ed. 2002, 41, 1363;
46. b) O. Navarro, R. A. Kelly, E. D. Stevens, S. P. Nolan, J. Am. Chem. Soc. 2003, 125, 16194;
47. c) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818;
48. Angew. Chem. Int. Ed. 2003, 42,