Modular access to alkylfluorides via radical decarboxylative-desulfonylative gem-difunctionalization.

Abstract

Fluorine-containing compounds hold pivotal importance in life sciences. Recent decades have witnessed significant research efforts toward developing practical fluorination methods. Radical-mediated decarboxylative fluorination has proven to be a robust approach for incorporating diverse monofluoroalkyl groups. Here we show a radical-mediated modular synthesis of alkyl fluorides through a decarboxylative-desulfonylative gem-difunctionalization under mild photochemical conditions. The multi-component reaction proceeds in a controlled sequence of radical decarboxylation and heteroaryl migration, governed by radical polarity and kinetic effects, resulting in a wide range of valuable alkyl fluorides. Two C-C bonds and one C-F bond are concurrently formed throughout the process. Both styrenes and aliphatic alkenes serve as suitable substrates for this transformation. Furthermore, this method can be applied to the incorporation of a monofluoroalkyl moiety into complex alkene molecules at a late stage.