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Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles.

ABSTRACT: The synthesis of gem-difluoroethylene compounds remains a difficult task in organic synthesis. Here, the direct difluoroethylation reactions of N- and O-nucleophiles including amides and acids were realized with a hypervalent iodine reagent: gem-difluorovinyl iodonium salt (DFVI). The reactions were accomplished via a neighbouring group rearrangement. The gem-difluorovinyl iodonium salt was found to display diverse reactivity due to its unique electronic effect and was applied to the incorporation of difluoroethylene group, including difluorovinylation of carboxylic acids, difluorovinylation and 1,3-cyclic fluorovinylation of amides and 1,1-cyclic difluoroethylation of amines.

SUBMITTER: Ge C

PROVIDER: S-EPMC9814539 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles.

Ge Chenxin C Wang Bin B Jiang Yunchen Y Chen Chao C

Communications chemistry 20221203 1

The synthesis of gem-difluoroethylene compounds remains a difficult task in organic synthesis. Here, the direct difluoroethylation reactions of N- and O-nucleophiles including amides and acids were realized with a hypervalent iodine reagent: gem-difluorovinyl iodonium salt (DFVI). The reactions were accomplished via a neighbouring group rearrangement. The gem-difluorovinyl iodonium salt was found to display diverse reactivity due to its unique electronic effect and was applied to the incorporati ...[more]

PMID: 36697903

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