Issue 45, 2024

Photoredox-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Abstract

An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the –CF2H group under mild conditions. This protocol utilized an easily accessible and inexpensive organophotocatalyst, offering the benefits of a broad substrate scope, good functional group tolerance, and good to excellent yields, in addition to a simple operational procedure. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that a radical pathway constitutes a single electron transfer (SET) procedure.

Graphical abstract: Photoredox-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Supplementary files

Article information

Article type
Paper
Submitted
29 Aug 2024
Accepted
07 Oct 2024
First published
08 Oct 2024

Org. Biomol. Chem., 2024,22, 8904-8915

Photoredox-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones

J. Yuan, H. Qu, W. Jia, J. Li, L. Yang, Y. Xiao, Y. Yin and L. Qu, Org. Biomol. Chem., 2024, 22, 8904 DOI: 10.1039/D4OB01413H

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