Methyl 3-oxo-ω-fluorosulfonylperfluoropentanoate: a versatile trifluoromethylating agent for organic halides

Abstract

Methyl 3-oxo-ω-fluorosulfonylperfluoropentanoate FSO₂CF₂CF₂OCF₂CO₂Me 1, prepared through the reaction of readily available ICF₂CF₂OCF₂CF₂SO₂F and SO₃ followed by MeOH, is a very convenient trifluoromethylating agent; in the presence of copper(I) iodide, 1not only reacts with vinyl, benzyl allyl, phenyl iodides and bromides, but also with aryl chlorides to give the corresponding trifluoromethyl compounds in moderate to high yield; a probable reaction mechanism is proposed.