Selectively Tunable Synthesis of ?-Trifluoromethyl Ketones

A cross-coupling of aldehydes and alpha-trifluoromethyl alkyl bromides was developed via dual nickel/photoredox catalysis system. A wide variety of substrates bearing a diverse set of functional groups were compatible to afford alpha-trifluoromethyl ketones under very mild conditions (visible light, ambient temperature, no strong base). Selectively tunable access to these ketones with the trifluoromethyl group on any one side can be smoothly obtained by simply modulating different reagents. Meanwhile, the asymmetric pattern was also investigated. Oy Br Rf O x v _H O Br\lambda R, Selective O T Rr O Rf

Automated summary

A cross-coupling reaction between aldehydes and alpha-trifluoromethyl alkyl bromides was successfully developed using a dual nickel/photoredox catalysis system. This reaction afforded alpha-trifluoromethyl ketones under mild conditions (visible light, ambient temperature, no strong base) with a wide range of substrates bearing various functional groups. The selectivity of the trifluoromethyl group on one side of the ketones can be modulated by different reagents, allowing for tunable access to these ketones.