Boronic Acids:  New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions

Jan H. Kirchhoff, Matthew R. Netherton, Ivory D. Hills, and Gregory C. Fu*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2002, 124 (46), pp 13662–13663
DOI: 10.1021/ja0283899
Publication Date (Web): October 23, 2002
Copyright © 2002 American Chemical Society
*

 Corresponding author. E-mail:  gcf@mit.edu.

Abstract

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The Suzuki reaction is an exceptionally useful cross-coupling process that has been widely applied in synthetic chemistry, and boronic acids are, by far, the most commonly employed coupling partner. To date, however, no versatile method has been developed for cross-coupling boronic acids with unactivated alkyl (as opposed to aryl or vinyl) electrophiles. This report describes a catalyst system that achieves this objective at room temperature. On the mechanistic side, this study demonstrates that Pd(P(t-Bu)2Me)2 undergoes oxidative addition under surprisingly mild conditions (0 °C). The resulting adduct is sufficiently stable toward β-hydride elimination that it can be structurally characterized, and it is a chemically competent intermediate in the cross-coupling process.

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History

  • Published In Issue November 20, 2002
  • Received September 3, 2002

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