Visible Light-Mediated Monofluoromethylation/Acylation of Olefins by Dual Organo-Catalysis.
Jiuli XiaYunliang GuoZhiguang LvJiaqiong SunGuangfan ZhengQian ZhangPublished in: Molecules (Basel, Switzerland) (2024)
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.