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Direct Synthesis of Pyrroles from Imines, Alkynes, and Acid Chlorides: An Isocyanide-Mediated Reaction

Daniel J. St. Cyr, Nicolas Martin and Bruce A. Arndtsen*

*Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada, Email: bruce.arndtsenmcgill.ca

D. J. St. Cyr, N. Martin, B. A. Arndtsen, Org. Lett., 2007, 9, 449-452.

DOI: 10.1021/ol062773j (free Supporting Information)


Abstract

A direct synthesis of pyrroles from imines, acid chlorides, and alkynes mediated by isocyanides proceeds with a range of substrates, providing a method to generate various pyrroles in high yield. Mechanistic studies suggest a generation of imino analogues of münchnones, which can undergo in situ coupling with alkynes to liberate isocyanate and form the pyrrole product.

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proposed mechanism



Key Words

Pyrroles, 1,3-dipolar cycloaddition


ID: J54-Y2007-0380