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Focus Article

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

A. D. Dilman, V. V. Levin

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: α-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.

Language: English

DOI: 10.1016/j.mencom.2015.07.001

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