FITS試薬の開発と新しいペルフルオロアルキル化反応の研究

抄録

Electrophilic perfluoroalkylations have been scarcely reported, though they are of great importance for introduction of perfluoroalkyl groups to organic compounds. It was found that FITS-m (m=10-2, 3i), synthesized by the reaction of bis (trifluoroacetoxy) -or difluoroiodoperfluoroalkaneswith benzene and trifluoromethanesulfonic acid, acted as highly reactive electrophilic perfluoro.alkylating agents. FITS underwent the first electrophilic reactions with carbanions, alkenes, alkynes, etc., and afforded many synthetic methods for perfluoroalkylated compounds, of which preparationswere difficult by the conventional, free radical or nucleophilic reactions.
Studies on the reactivity of FITS led to fortultous discovery of oxy_perfluoroalkylation, a newtype of oxygenation, which made it possible. to prepare perfluoroalkylated carbonyl compoundsdirectly from alkenes under oxygen atmosphere.
Effective use of the fluorine atoms in the perfluoroalkyl groups as an application of FITS-2 or 3i provided a new synthetic approach to trifluoromethyl-compounds with various functionalgroups.