Gold(I)-Catalyzed Intramolecular Acetylenic Schmidt Reaction

David J. Gorin, Nicole R. Davis, and F. Dean Toste*
Department of Chemistry, University of California, Berkeley, California 94720
J. Am. Chem. Soc., 2005, 127 (32), pp 11260–11261
DOI: 10.1021/ja053804t
Publication Date (Web): July 23, 2005
Copyright © 2005 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.

, fdtoste@berkeley.edu

Abstract

Abstract Image

Substituted pyrroles were prepared by a gold(I)-catalyzed acetylenic Schmidt reaction of homopropargyl azides. The reaction allows for regiospecific substitution at each position of the pyrrole ring under mild conditions. A mechanism in which azides serve as nucleophiles toward gold(I)-activated alkynes with subsequent gold(I)-aided expulsion of dinitrogen is proposed.

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History

  • Published In Issue August 17, 2005
  • Received June 10, 2005

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