Palladium(0)-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Potassium Aryl- and Heteroaryltrifluoroborates with Alkenyl Bromides

Gary A. Molander* and Tiziano Fumagalli
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
J. Org. Chem., 2006, 71 (15), pp 5743–5747
DOI: 10.1021/jo0608366
Publication Date (Web): June 24, 2006
Copyright © 2006 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

Efficient palladium(0)-catalyzed Suzuki−Miyaura cross-couplings are described. The reactions involving potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides can generally be carried out using ≤2 mol % of palladium catalyst and 3 equiv of base in toluene/H2O. When stereodefined alkenyl bromides are employed, the resulting styrene derivatives are accessed stereospecifically. A variety of functional groups are tolerated in both coupling partners.

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History

  • Published In Issue July 21, 2006
  • Received April 20, 2006

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