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Published on: September 7, 2011
Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction
David J Gorin1, Nicole R Davis, F Dean Toste
1Department of Chemistry, University of California, Berkeley, California 94720, USA.
Abstract:
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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