A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology

Riina K. Arvela,† Nicholas E. Leadbeater,*† Michael S. Sangi,† Victoria A. Williams,† Patricia Granados,‡ and Robert D. Singer‡
Department of Chemistry, University of Connecticut, Unit 3060, 55 North Eagleville Road, Storrs, Connecticut 06269-3060, and Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia B3H 3C3, Canada
J. Org. Chem., 2005, 70 (1), pp 161–168
DOI: 10.1021/jo048531j
Publication Date (Web): December 8, 2004
Copyright © 2005 American Chemical Society
†

 University of Connecticut.

,
*

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

,
‡

 Saint Mary's University.

, nicholas.leadbeater@uconn.edu

Abstract

Abstract Image

We present here a reassessment of our transition-metal free Suzuki-type coupling protocol. We believe that, although the reaction can be run without the need for addition of a metal catalyst, palladium contaminants down to a level of 50 ppb found in commercially available sodium carbonate are responsible for the generation of the biaryl rather than, as previously suggested, an alternative non-palladium-mediated pathway. We present a revised methodology for Suzuki couplings using ultralow palladium concentrations for use with aryl and vinyl boronic acids and discuss the effects of the purity of the boronic acid on the reaction.

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History

  • Published In Issue January 07, 2005
  • Received August 20, 2004

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