A novel synthesis of functionalized 1,1-difluoro-1-alkenes via isolable 2,2-difluorovinylsilanes

Various 1,1-difluoro-1-alkenes such as monosubstituted 1,1-difluoro-1-alkenes, 2-bromo-1,1-difluoro-1-alkenes, and 1,1-difluoro-3-hydroxy-1-alkenes are prepared in two simple steps from 1-trifluoromethylvinylsilane: (i) its S(N)2' reaction with nucleophiles to construct 2.2-difluorovinylsilanes and (ii) the subsequent substitution of electrophiles for the vinylic silyl group. (C) 2003 Elsevier Science Ltd. All rights reserved.