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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, Email:

D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc., 2005, 127, 11260-11261.

DOI: 10.1021/ja053804t (free Supporting Information)


A mild, gold(I)-catalyzed acetylenic Schmidt reaction of homopropargyl azides gave regiospecific substituted pyrroles. 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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proposed mechanism

Key Words

Azides, Pyrroles, Schmidt Reaction

ID: J48-Y2005-2540