A facile synthesis of trifluoromethyl- and 3,3,3-trifluoropropenyl- substituted aromatic compounds by the oxidative desulfurization-fluorination of the corresponding carbodithioates

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.