Unexpected reactivity of cyclic perfluorinated iodanes with electrophiles

Abstract

We have found that cyclic perfluorinated iodanes react with electrophiles (E⁺ = Br, Cl, F, I) to afford perfluorinated E–R_F compounds. This reactivity is unexpected since cyclic perfluorinated iodanes are considered as electrophilic reagents that normally react with nucleophiles (e.g. Nu⁻ = SR, OR) to afford Nu–R_F products. The utility of this new transformation is demonstrated for a [¹⁸F]CF₃CF₂-containing compound which was prepared from [¹⁸F]XeF₂ obtained from cyclotron produced [¹⁸F]fluoride.