The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles:  Sonogashira Reactions of Unactivated Alkyl Bromides and Iodides

Matthias Eckhardt and Gregory C. Fu*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2003, 125 (45), pp 13642–13643
DOI: 10.1021/ja038177r
Publication Date (Web): October 17, 2003
Copyright © 2003 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.

, gcf@mit.edu

Abstract

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A Pd/N-heterocyclic carbene-based catalyst achieves the Sonogashira coupling of an array of functionalized, β-hydrogen-containing alkyl bromides and iodides under mild conditions. By furnishing the first example of a nonphosphine-based palladium catalyst for cross-coupling unactivated alkyl electrophiles, this study provides an impetus for future efforts at catalyst development that extend beyond phosphine ligands.

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History

  • Published In Issue November 12, 2003
  • Received August 28, 2003

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