Merging Copper(I) Photoredox Catalysis and Iodine(III) Chemistry for the Oxy-monofluoromethylation of Alkenes

A simple process for the oxy-monofluoromethylation of alkenes is described. In combination with visible-light copper(I) photoredox catalysis, an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands serves as a powerful source of a monofluoromethyl (CH2F) radical, enabling the step economical synthesis of gamma-fluoro-acetates from a broad range of olefinic substrates under mild conditions. Applications to late-stage diversification of alkenes derived from complex molecules, amino acids and the synthesis of fluoromethylated heterocycles are also demonstrated.

Automated summary

A simple process for the oxy-monofluoromethylation of alkenes is presented. The use of visible-light copper(I) photoredox catalysis, in combination with an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands, enables the synthesis of gamma-fluoro-acetates from various olefinic substrates under mild conditions. The study also demonstrates its applications in late-stage diversification of complex molecules, amino acids, and the synthesis of fluoromethylated heterocycles.