Issue 15, 2023

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 C2[double bond, length as m-dash]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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
06 Apr 2023
Accepted
21 Jun 2023
First published
24 Jun 2023

Org. Chem. Front., 2023,10, 3875-3882

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

W. Xu, B. Cheng, Y. Zhang, L. Fang, H. Zhai, C. Wang and T. Wang, Org. Chem. Front., 2023, 10, 3875 DOI: 10.1039/D3QO00505D

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