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
Org. Lett., 2007, 9 (3), pp 449–452
DOI: 10.1021/ol062773j
Publication Date (Web): January 13, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, bruce.arndtsen@mcgill.ca

Abstract

Abstract Image

A direct synthesis of pyrroles from imines, acid chlorides, and alkynes mediated by isocyanides is reported. This reaction proceeds with a range of each of these three substrates, providing a method to generate families of pyrroles in high yield. Mechanistic studies suggest this process proceeds via the generation of imino analogues of münchnones, which can undergo in situ coupling with alkynes to liberate isocyanate and form the pyrrole product.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue February 01, 2007
  • Received November 14, 2006

Recommend & Share

Related Content

Other ACS content by these authors: