Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents

alpha-Fluorinated organosilanes Me3SiCF2X serve as versatile reagents for the synthesis of organofluorine compounds. Most reactions start from Lewis base activation of carbon silicon bond through the intermediacy of five-coordinate siliconate species. Interaction of these silanes with suitable electrophiles leads to products of nucleophilic fluoroalkylation; an alternative pathway involves generation of difluorocarbene. These reagents can also be considered as equivalents of difluoromethylene radical anion and bis(carbanion) when carbon-heteroatom bond C-X is activated.