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Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors.

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A cascade strategy to synthesise gem-difluorinated 2H-furans from reactions of BrCF2CO2Et with enaminones has been described. The reactions tolerate a wide variety of functional groups under metal-free conditions. An active… Click to show full abstract

A cascade strategy to synthesise gem-difluorinated 2H-furans from reactions of BrCF2CO2Et with enaminones has been described. The reactions tolerate a wide variety of functional groups under metal-free conditions. An active aminocyclopropane is proposed to be a key intermediate through the cyclopropanation of difluorocarbene with enaminones, which further triggers a regioselective C-C bond cleavage in situ to afford the corresponding gem-difluorinated 2H-furans.

Keywords: gem difluorinated; gem; metal free; free synthesis; synthesis gem; difluorinated heterocycles

Journal Title: Chemical communications
Year Published: 2022

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