RECENT PROGRESS IN PERFLUOROALKYLATION BY RADICAL SPECIES WITH SPECIAL REFERENCE TO THE USE OF BIS(PERFLUOROALKANOYL) PEROXIDES

Radical species play important roles in perfluoroalkylation, so recent advances in perfluoroalkylation with radical intermediates are reviewed from two aspects; one is thermal and photochemical generations of perfluoroalkyl radicals and the other is via electron transfer. Especially, in this article, perfluoroalkylations with bis(perfluoroalkanoyl) peroxides via electron transfer developed in our laboratory are discussed in detail and compared with methods using other reagents. Organofluorine compounds often show unique properties [1], and are widely used as medicines, pesticides, dyes or surfactants. Especially the substitution by perfluoroalkyl group at particular positions of organic compounds may give rise to unique physical or biological properties which cannot be achieved by incorporating other functional groups. However, the methods for the introduction of perfluoroalkyl groups into organic compounds have not yet been well established. Although nucleophilic substitution via cationic intermediates is the most important and common reaction in hydrocarbon chemistry, the generation of perfluoroalkyl cationic intermediates is very difficult due to the strong electronegativity of fluorine [2] (Scheme 1).{A figure is presented}. © 1990.