Visible Light-Mediated Monofluoromethylation/Acylation of Olefins by Dual Organo-Catalysis.

Monofluoromethyl (CH(2)F) motifs exhibit unique bioactivities and are considered privileged units in drug discovery. The radical monofluoromethylative difunctionalization of alkenes stands out as an appealing approach to access CH(2)F-containing compounds. However, this strategy remains largely underdeveloped, particularly under metal-free conditions. In this study, we report on visible light-mediated three-component monofluoromethylation/acylation of styrene derivatives employing NHC and organic photocatalyst dual catalysis. A diverse array of α-aryl-β-monofluoromethyl ketones was successfully synthesized with excellent functional group tolerance and selectivity. The mild and metal-free CH(2)F radical generation strategy from NaSO(2)CFH(2) holds potential for further applications in fluoroalkyl radical chemistry.