Heck-type coupling vs. conjugate addition in phosphine-rhodium catalyzed reactions of aryl boronic acids with α,β-unsaturated carbonyl compounds: A systematic investigation

Dalton Transactions

Volumn , Issue 28, 2007, Pages 3055-3064

  Zou, Gang ^a   Guo, Jianping ^a,b   Wang, Zhiyong ^a   Huang, Wen ^a,b   Tang, Jie ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; LIGANDS; PH EFFECTS; PHOSPHORUS COMPOUNDS; REACTION KINETICS; RHODIUM;

ARYL BORONIC ACIDS; BIPHASIC SYSTEMS; CARBONYLS;

ORGANIC ACIDS;

EID: 34547243856     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b615473e     Document Type: Article

References (36)

1. K. Yoshida and T. Hayashi, in: Modern Rhodium-Catalyzed Organic Reactions, ed., P. A. Evans, Wiley-VCH, Weinheim, 2005, pp. 55-78
2. K. Yoshida and T. Hayashi, in Boronic Acids, ed., D. G. Hall, Wiley-Vch Verlag GmbH & Co. KGaA, Weinheim, 2005, pp. 171-203
3. T. Hayashi Pure Appl. Chem. 2004 76 465 475
4. T. Hayashi K. Yamasaki Chem. Rev. 2003 103 2829 2844
5. K. Fagnou M. Lautens Chem. Rev. 2003 103 169 196
6. T. Hayashi Synlett 2001 879 887
7. M. Sakai H. Hayashi N. Miyaura Organometallics 1997 16 4229 4231
8. Y. Takaya M. Ogasawara T. Hayashi M. Sakai N. Miyaura J. Am. Chem. Soc. 1998 120 5579 5580
9. M. Kuriyama K. Nagai K. Yamada Y. Miwa T. Taga K. Tomioka J. Am. Chem. Soc. 2002 124 8932 8939
10. J.-F. Paquin C. Defieber C. R. J. Stephenson E. M. Carreira J. Am. Chem. Soc. 2005 127 10850 10851
11. R. Shintani W. Duan T. Nagano A. Okada T. Hayashi Angew. Chem., Int. Ed. 2005 44 4611 4614
12. T. Hayashi M. Takahashi Y. Takaya M. Ogasawara J. Am. Chem. Soc. 2002 124 5052 5058
13. A. Kina H. Iwamura T. Hayashi J. Am. Chem. Soc. 2006 128 3904 3905
14. E. J. Farrington J. M. Brown C. F. J. Barnard E. Rowsell Angew. Chem., Int. Ed. 2002 41 169 171
15. T. Koike X. Du T. Sanada Y. Danda A. Mori Angew. Chem., Int. Ed. 2003 42 89 92
16. C. S. Cho S. Uemura J. Organomet. Chem. 1994 465 85 92
17. X. Du M. Suguro K. Hirabayashi A. Mori T. Nishikata N. Hagiwara K. Kawata T. Okeda H. F. Wang K. Fugami M. Kosugi Org. Lett. 2001 3 3313 3316
18. M. M. S. Andappan P. Nilsson M. Larhed Chem. Commun. 2004 218 219
19. A. Mori Y. Danda T. Fujii K. Hirabayashi K. Osakada J. Am. Chem. Soc. 2001 123 10774 10775
20. T. Yoshida T. Okano Y. Ueda S. Otsuka J. Am. Chem. Soc. 1981 103 3411 3422
21. M. Lautens A. Roy K. Fukuoka K. Fagnou B. Martín-Matute J. Am. Chem. Soc. 2001 123 5358 5359
22. C. Bianchini C. Mealli A. Meli D. M. Proserpio M. Peruzzini F. Vizza P. Frediani J. Organomet. Chem. 1989 369 C6 C10
23. J. Ott L. M. Venanzi C. A. Ghilardi S. Midollini A. Orlandini J. Organomet. Chem. 1985 291 89 100
24. G. Zou Z. Wang J. Zhu J. Tang Chem. Commun. 2003 2438 2439
25. L. Navarre S. Darses J.-P. Genet Chem. Commun. 2004 1108 1109
26. L. Navarre S. Darses J.-P. Genet Adv. Synth. Catal. 2006 348 317 322
27. M. Lautens J. Mancuso H. Grover Synthesis 2004 2006 2014
28. J. L. Gras K. J. Gombatz G. Buchi Org. Synth. 1981 60 88 90
29. A. Fürstner H. Krause Adv. Synth. Catal. 2001 343 343 350
30. P. Dierkes P. W. N. M. Leeuwen J. Chem. Soc., Dalton Trans. 1999 1519 1529
31. Z. Freixa P. W. N. M. Leeuwen Dalton Trans. 2003 1890 1901
32. Z. Wang G. Zou J. Tang Chem. Commun. 2004 1192 1193
33. A. Abiko Acc. Chem. Res. 2004 37 387 395
34. Y. Mori K. Manabe S. Kobayashi Angew. Chem., Int. Ed. 2001 40 2815 2818
35. Y. Mori J. Kobayashi K. Manabe S. Kobayashi Tetrahedron 2002 58 8263 8268
36. K. Yoshida M. Ogasawara T. Hayashi J. Org. Chem. 2003 68 1901 1905