1-Trifluoromethylvinylsilane as a CF2C-−CH2+ Synthon: Synthesis of Functionalized 1,1-Difluoro-1-alkenes via Isolable 2,2-Difluorovinylsilanes
- 4 September 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (20) , 7800-7805
- https://doi.org/10.1021/jo034718j
Abstract
Various 1,1-difluoro-1-alkenes such as monosubstituted 1,1-difluoro-1-alkenes, 2-bromo-1,1-difluoro-1-alkenes, and 3,3-difluoroallylic alcohols are synthesized in two simple steps from 1-trifluoromethylvinylsilane: (i) its SN2' reaction with nucleophiles to construct 2,2-difluorovinylsilanes and (ii) the subsequent substitution of electrophiles for the vinylic silyl group. The combination of these two processes allows a one-pot synthesis of the functionalized 1,1-difluoro-1-alkenes starting from 1-trifluoromethylvinylsilane, which functions as a CF2=C(-)-CH2+ synthon.Keywords
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