A copper-catalyzed synthesis of pyrroles through photochemically generated acylazirines

Abstract

A synthesis of highly substituted 2,4-diacylpyrroles through a Cu-catalyzed dimerization of acylazirines generated in situ by a photochemical valence isomerization is described. The shown methodology allows the use of simple precursors and a readily available copper(II)-catalyst. Since the reaction is best performed at elevated temperatures, a method to adjust the temperature of the reaction mixture during this dual light and metal-induced process was established. Additionally, mechanistic studies of the reaction were performed in order to provide a deeper understanding of the chemistry of 2-acylazirines.