Suzuki−Miyaura Cross-Coupling Reactions of Potassium Vinyltrifluoroborate with Aryl and Heteroaryl Electrophiles

Gary A. Molander* and Adam R. Brown
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 191046323
J. Org. Chem., 2006, 71 (26), pp 9681–9686
DOI: 10.1021/jo0617013
Publication Date (Web): December 1, 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

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We have previously reported that the palladium-catalyzed cross-coupling reaction of potassium vinyltrifluoroborate with aryl electrophiles proceeds with good yields. Herein, we describe recent progress in optimizing the reaction, as well as outlining the scope and limitations of the reaction. The cross-coupling reaction can generally be effected using 2 mol % of PdCl2 and 6 mol % of PPh3 as a catalyst system in THF/H2O with Cs2CO3 as a base. Moderate to good yields are obtained in the presence of a variety of functional groups.

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History

  • Published In Issue December 22, 2006
  • Received August 16, 2006

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