Trifluoromethyl-substituted aromatic compounds were easily synthesized by the oxidative desulfurization-fluorination reaction of readily accessible methyl arenecarbodithioates using [n-Bu4N]H2F3 and 1,3-dibromo-5,5-dimethylhydantoin (DBH) under extremely mild conditions. Use of N-bromosuccinimide or N-iodosuccinimide instead of DBH afforded difluoro(methylthio)methyl-substituted aromatics. In a similar way, 3,3,3-trifluoropropenyl-substituted aromatic compounds were readily prepared from the corresponding α,β-unsaturated carbodithioates.
1 July 1995 in Bulletin of the Chemical Society of Japan
When CFBr3 was treated with n-BuLi at -130 °C, thermally labile LiCFBr2 was generated which reacted smoothly with a coexisting electrophile RR’CO to give an adduct RR’C(OH)CFBr2 in good yield.