Iron-catalyzed [3 + 2]-cycloaddition of in situ generated N-ylides with alkynes or olefins: access to multi-substituted/polycyclic pyrrole derivatives

Abstract

An iron-catalyzed one-pot three-component reaction of 1-substituted benzimidazoles with diazoacetates and electron-deficient alkynes or alkenes has been reported. Mechanistically, the reaction goes through a 1,3-dipolar cycloaddition of catalytically generated benzimidazolium N-ylides with various activated alkynes or alkenes, leading to multi-substituted and polycyclic fused pyrrole derivatives, respectively.