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: fdtoste
berkeley.edu
D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc., 2005, 127, 11260-11261.
DOI: 10.1021/ja053804t
Abstract
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.
see article for more examples
proposed mechanism
Key Words
Azides, Pyrroles, Schmidt Reaction
ID: J48-Y2005-2540
