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

[Bis(monofluoroacetoxy)iodo]benzene, an efficient and alternative reagent for radical monofluoromethylation under visible-light copper(I) photoredox catalysis, provides access to CH₂F-containing organic compounds. The broad utility of this radical monofluoromethylating reagent in alkene oxy-monofluoromethylation reactions, including for the synthesis of fluoromethylated amino acid derivatives and heterocycles, is demonstrated.

Abstract

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 γ-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.

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