Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction.
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.
Gorin
David J
DJ
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Davis
Nicole R
NR
Toste
F Dean
FD