Introduction of a pentafluorophenyl group into perfluoro olefins by trimethyl(pentafluorophenyl)silane in the presence of cesium fluoride.

Abstract

Perfluorophenylation of CF2:CFCF2C6F5 with C6F5SiMe3 in the presence of CsF afforded products of side-chain arylation exclusively: Z- and E-C6F5CF:CFCF2C6F5 in 39% yield (1:1.6, resp.). Pentafluorophenylation of once-arylated substrate occurs with CF2:CFCF3, with the formation of Z- and E-4-(C6F5)C6F4CF:CFCF3 in 54% yields (1.4:1, resp.). More rigorous conditions are required for the pentafluorophenylation of internal perfluoro alkenes than for terminal compds. [on SciFinder(R)]