Palladium/tris(tert-butyl)phosphine-catalyzed Suzuki cross-couplings in the presence of water

Advanced Synthesis and Catalysis

Volumn 352, Issue 11-12, 2010, Pages 2081-2084

  Lou, Sha ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Boron; Cross coupling; Halides; Palladium; Water

Indexed keywords

EID: 77956369284     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000267     Document Type: Article

References (25)

1. For leading references, see: G. C. Fu, Acc. Chem. Res. 2008, 41, 1555-1564.
2. For reviews, see: a) Metal-Catalyzed Cross-Coupling Reactions, (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, New York, 2004
3. b) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E.-i. Negishi), Wiley-Interscience, New York, 2002.
4. 3- and Pd/PCy3-catalyzed Suzuki reactions, see: a) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587
5. Angew. Chem. Int. Ed. 1998, 37, 3387-3388
6. b) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028
7. c) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298
8. d) N. Kudo, M. Perseghini, G. C. Fu, Angew. Chem. 2006, 118, 1304-1306
9. Angew. Chem. Int. Ed. 2006, 45, 1282-1284.
10. 3-catalyzed Suzuki reactions, see: a) T. Amaya, T. Nakata, T. Hirao, J. Am. Chem. Soc. 2009, 131, 10810-10811
11. b) W. Huang, L. Su, Z. Bo, J. Am. Chem. Soc. 2009, 131, 10348-10349
12. c) H. Ihara, M. Suginome, J. Am. Chem. Soc. 2009, 131, 7502-7503.
13. For an example of related, independent observations by others, see: A. Antoft-Finch, T. Blackburn, V. Snieckus, J. Am. Chem. Soc. 2009, 131, 17750-17752.
14. For an overview of boronic acids, see: Boronic Acids, (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2005.
15. [3d]).
16. 3-catalyzed Suzuki reactions, see: a) R. T. Lewis, W. P. Blackaby, T. Blackburn, A. S. R. Jennings, A. Pike, R. A. Wilson, D. J. Hallett, S. M. Cook, P. Ferris, G. R. Marshall, D. S. Reynolds, W. F. A. Sheppard, A. J. Smith, B. Sohal, J. Stanley, S. J. Tye, K. A. Wafford, J. R. Atack, J. Med. Chem. 2006, 49, 2600-2610
17. b) S. T. Handy, D. Mayi, Tetrahedron Lett. 2007, 48, 8108-8110
18. c) M. J. Fray, A. T. Gillmore, M. S. Glossop, D. J. McManus, I. B. Moses, C. F. B. Praquin, K. A. Reeves, L. R. Thompson, Org. Process Res. Dev. 2010, 14, 263-271.
19. 2O ($100/500 g).
20. [3b]
21. 4 can be exposed to air for seven months without a change in its activity as a Suzuki cross-coupling catalyst
22. 4 results in a slower reaction.
23. b) A gramscale reaction (entry 1 of Table 2) proceeded in 97% yield (1.14 g).
24. 1H NMR spectroscopy, the addition of water to the "dried" arylboronic acid in THF at room temperature led to rapid formation of the arylboronic acid.
25. [3d] is more effective than the method provided in Eq. (2).