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 C2 =C3, 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. © 2023 The Royal Society of Chemistry.