Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides

Gary A. Molander* and Luciana A. Felix
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
J. Org. Chem., 2005, 70 (10), pp 3950–3956
DOI: 10.1021/jo050286w
Publication Date (Web): April 13, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, gmolandr@sas.upenn.edu

Abstract

Abstract Image

The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)2, 10 mol % of PPh3, and 3 equiv of Cs2CO3 in THF−H2O (10:1). A variety of functional groups are tolerated in both coupling partners.

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History

  • Published In Issue May 13, 2005
  • Received February 14, 2005

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