From benzopyrroles to phenylpyrroles: remodeling of indoles enabled by photoredox catalysis

Abstract

A facile approach toward 3-(o-aminophenyl)pyrroles was developed by remodeling of N-sulfonyl-3-acyl indoles with N-phenylglycines under photoredox catalysis. This strategy enables the conversion of a fused bicyclic system into a biaryl scaffold, mechanically involving a Giese-type radical addition to C2C3, C2–N cleavage of the resulting indoline skeleton, and generation of a new pyrrole motif. This novel methodology provides an innovative strategy for the synthesis of potentially valuable 3-(o-aminophenyl)pyrroles and related alkaloids.