Photoredox‐Catalyzed Three‐Component Difluoroalkylation of Quinoxalin‐2(1H)‐ones with Unactivated Vinylarenes and [Ph3PCF2H]+Br

An efficient synthesis of a variety of 3‐difluoroalkyl quinoxalin‐2(1H)‐ones via a photoredox‐catalyzed three‐component reaction between quinoxalin‐2(1H)‐ones, vinylarenes, with inexpensive and easily accessible difluoromethyltriphenyl phosphonium bromide salt as the difluoromethylated reagent is de...

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Veröffentlicht in:Asian journal of organic chemistry 2023-11, Vol.12 (11), p.n/a
Hauptverfasser: Xu, Yuandong, Qu, Hongzhao, Yuan, Jinwei, Guo, Na, Yang, Liangru, Yin, Yanli, Qu, Lingbo, Mao, Jian
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Sprache:eng
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Zusammenfassung:An efficient synthesis of a variety of 3‐difluoroalkyl quinoxalin‐2(1H)‐ones via a photoredox‐catalyzed three‐component reaction between quinoxalin‐2(1H)‐ones, vinylarenes, with inexpensive and easily accessible difluoromethyltriphenyl phosphonium bromide salt as the difluoromethylated reagent is described. This protocol shows excellent reactivity, providing a wide range of difluoroalkyl‐substituted quinoxalin‐2(1H)‐ones in moderate to excellent yields under mild conditions. A difluoroalkyl radical intermediate was involved in this three‐component transformation. A photocatalytic oxidative protocol for the synthesis of 3‐difluoroalkyl quinoxalin‐2(1H)‐ones derivatives was developed via the difluoroalkylation of quinoxalin‐2(1H)‐ones with unactivated vinylarenes and [Ph3PCF2H]+Br−.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300405