General Approach to the Coupling of Organoindium Reagents with Imines via Copper Catalysis

Daniel A. Black and Bruce A. Arndtsen*
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
Org. Lett., 2006, 8 (10), pp 1991–1993
DOI: 10.1021/ol060277p
Publication Date (Web): April 12, 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.

, bruce.arndtsen@mcgill.ca

Abstract

Abstract Image

A copper-catalyzed three-component coupling of organoindium reagents with imines and acid chlorides is described. This mild carbon−carbon bond forming reaction requires only one-third of an equivalent of indium reagent to proceed in high yield, with the sole byproduct being indium trichloride. The reaction demonstrates broad generality, with aryl-, heteroaryl-, vinyl-, and alkylindiums, as well as functionalized imines and acid chlorides, all providing α-substituted amides or N-protected amines in a single step.

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History

  • Published In Issue May 11, 2006
  • Received February 1, 2006

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