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

An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF H-substituted benzimidazo[2,1- ]isoquinolin-6(5 )-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the -CF H group under mild conditions. This protoco...

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Veröffentlicht in:Organic & biomolecular chemistry 2024-11, Vol.22 (45), p.8904-8915
Hauptverfasser: Yuan, Jinwei, Qu, Hongzhao, Jia, Wenfeng, Li, Jinling, Yang, Liangru, Xiao, Yongmei, Yin, Yanli, Qu, Lingbo
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF H-substituted benzimidazo[2,1- ]isoquinolin-6(5 )-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the -CF H 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob01413h