Photoredox catalyzed difluoro(phenylthio)methylation of 2,3-allenoic acids with {difluoro(phenylthio)methyl}triphenylphosphonium triflate

•New applications of fluoroalkylphosphonium salts.•(Phenylthio)difluoromethylation of 2,3-allenoic acids.•Tandem radical addition/intramolecular reaction.•Facile synthesis of (phenylthio)difluoromethylated butenolides. The photoredox catalyzed difluoro(phenylthio)methylation of 2,3-allenoic acids wi...

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Veröffentlicht in:Journal of fluorine chemistry 2022-05, Vol.257-258, p.109969, Article 109969
Hauptverfasser: Zhu, Yao-Yao, Liu, Shuai, Huang, Yangen, Qing, Feng-Ling, Xu, Xiu-Hua
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Sprache:eng
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Zusammenfassung:•New applications of fluoroalkylphosphonium salts.•(Phenylthio)difluoromethylation of 2,3-allenoic acids.•Tandem radical addition/intramolecular reaction.•Facile synthesis of (phenylthio)difluoromethylated butenolides. The photoredox catalyzed difluoro(phenylthio)methylation of 2,3-allenoic acids with {difluoro(phenylthio)methyl}triphenylphosphonium triflate was investigated. A series of 4-aryl-2,3-allenoic acids underwent tandem radical difluoro(phenylthio)methylation/intramolecular cyclization to afford previously unknown 4-difluoro(phenylthio)methylated butenolides, which could be converted to the corresponding difluoro(phenylthio)methylated furan-2(3H)-one and difluoro(phenylsulfonyl)methylated butenolide derivatives. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2022.109969