Synthesis of tetrafluoroethyl- and tetrafluoroethylene-containing amines by the reaction of silanes with enamines under acidic conditions

• PhSCF2CF2TMS and PhSO2CF2CF2TMS react with iminium salts formed from enamines and HF to form products of nucleophilic addition.
• Radical or reductive desulfurization of the adducts affords amines with the tetrafluoroethyl group.
• Primary, secondary and tertiary amines substituted with the CF2CF2 group on α-carbon are accessed by this method.

Enamines with in situ formed hydrogen fluoride underwent efficient reaction with trimethyl(1,1,2,2-tetrafluoro-2-(phenylthio)ethyl)silane and trimethyl(1,1,2,2-tetrafluoro-2-(phenylsulfonyl)ethyl)silane. Radical or reductive desulfurization of the addition products provided amines containing the tetrafluoroethyl group.

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