Hydroxylated terphenylphosphine ligands for palladium-catalyzed ortho-selective cross-coupling of dibromophenols, dibromoanilines, and their congeners with Grignard reagents

Tetrahedron

Volumn 67, Issue 52, 2011, Pages 10156-10163

  Ishikawa, Shunpei ^a,c   Manabe, Kei ^a,b  

^a RIKEN   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

^c OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Cross coupling; Grignard reagent; Palladium; Phosphine; Site selective

Indexed keywords

BROMINE DERIVATIVE; DIBROMOANILINE DERIVATIVE; DIBROMOPHENOL DERIVATIVE; GRIGNARD REAGENT; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; TERPHENYLPHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CROSS COUPLING REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 82255179467     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.013     Document Type: Article

References (39)

1. A. de Meijere, and F. Diederich Metal-Catalyzed Cross-Coupling Reactions 2nd ed. 2004 Wiley-VCH Weinheim
2. S. Schröter, C. Stock, and T. Bach Tetrahedron 61 2005 2245
3. I.J.S. Fairlamb Chem. Soc. Rev. 36 2007 1036
4. J.-R. Wang, and K. Manabe Synthesis 2009 1405
5. R. Singh, and G. Just J. Org. Chem. 54 1989 4453
6. Y. Ishii, N. Chatani, S. Yorimitsu, and S. Murai Chem. Lett. 27 1998 157
7. S.M. Dirk, D.W. Price Jr., S. Chanteau, D.V. Kosynkin, and J.M. Tour Tetrahedron 57 2001 5109
8. T. Schaub, M. Backes, and U. Radius J. Am. Chem. Soc. 128 2006 15964
9. L. Ackermann, and A. Althammer Angew. Chem., Int. Ed. 46 2007 1627
10. I.N. Houpis, J.-P.V. Hoeck, and U. Tilstam Synlett 2007 2179
11. F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, and S. Murai J. Am. Chem. Soc. 126 2004 2706
12. K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S.-i. Kodama, I. Nakajima, A. Minato, and M. Kumada Bull. Chem. Soc. Jpn. 49 1976 1958
13. D.J. Sinclair, and M.S. Sherburn J. Org. Chem. 70 2005 3730
14. C.-G. Dong, and Q.-S. Hu J. Am. Chem. Soc. 127 2005 10006
15. S. Ishikawa, and K. Manabe Chem. Lett. 36 2007 1304
16. S. Ishikawa, and K. Manabe Org. Lett. 9 2007 5593
17. S. Ishikawa, and K. Manabe Angew. Chem., Int. Ed. 49 2010 772
18. S. Ishikawa, and K. Manabe Chem. Lett. 36 2007 1302
19. S. Ishikawa, and K. Manabe Tetrahedron 66 2010 297
20. D.W. Old, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 9722
21. J.P. Wolfe, and S.L. Buchwald Angew. Chem., Int. Ed. 38 1999 2413
22. X. Huang, K.W. Anderson, D. Zim, L. Jiang, A. Klapars, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 6653
23. T. Hayashi, T. Mise, and M. Kumada Tetrahedron Lett. 17 1976 4351
24. Y. Hatanaka, K. Goda, F. Yamashita, and T. Hiyama Tetrahedron Lett. 35 1994 7981
25. K. Matsui, S. Takizawa, and H. Sasai Synlett 2006 761
26. X. Meng, Y. Huang, and R. Chen Chem. - Eur. J. 14 2008 6852
27. N. Yoshikai, H. Matsuda, and E. Nakamura J. Am. Chem. Soc. 131 2009 9590
28. M.R. Netherton, and G.C. Fu Org. Lett. 3 2001 4295
29. J. Blum, O. Berlin, D. Milstein, Y. Ben-David, B.C. Wassermann, S. Schutte, and H. Schumann Synthesis 2000 571
30. J. Terao, A. Ikumi, H. Kuniyasu, and N. Kambe J. Am. Chem. Soc. 125 2003 5646
31. X. Mei, A.T. August, and C. Wolf J. Org. Chem. 71 2006 142
32. T. Wang, B.J. Alfonso, and J.A. Love Org. Lett. 9 2007 5629
33. M. Arisawa, T. Suzuki, T. Ishikawa, and M. Yamaguchi J. Am. Chem. Soc. 130 2008 12214
34. J.-R. Wang, and K. Manabe Org. Lett. 11 2009 741
35. L. Boymond, M. Rottländer, G. Cahiez, and P. Knochel Angew. Chem., Int. Ed. 37 1998 1701
36. S. Ishikawa, and K. Manabe Chem. Lett. 38 2009 1206
37. Similar conformational effects of 2,6-dihydroxyphenyl groups have been reported for artificial receptors: K. Manabe, K. Okamura, T. Date, and K. Koga J. Org. Chem. 58 1993 6692
38. A. Jutand Chem. Rev. 108 2008 2300
39. F. Barrios-Landeros, B.P. Carrow, and J.F. Hartwig J. Am. Chem. Soc. 131 2009 8141