Visible-Light-Induced Monofluoroalkenylation and <i>gem</i>-Difluoroallylation of Inactivated C(sp<sup>3</sup>)–H Bonds via 1,5-Hydrogen Atom Transfer (HAT)
Yanyang Bao, Meifang Tang, Qing Wang, Zhong‐Yan Cao, Yanan Wang, Zheliang Yuan
Abstract
The direct monofluoroalkenylation of C(sp 3 )–H bonds is of great importance and quite challenging. Current methods have been restricted to the monofluoroalkenylation of activated C(sp 3 )–H bonds. Here, we reported the photocatalyzed C(sp 3 )–H monofluoroalkenylation of inactivated C(sp 3 )–H bonds with gem -difluoroalkenes via 1,5-hydrogen atom transfer. This process shows good functional group tolerance, such as halides (F, Cl), nitrile, sulfone, ester, and pyridine, and good γ-selectivity. Moreover, this method succeeds in the photocatalyzed gem -difluoroallylation of inactivated C(sp 3 )–H with α-trifluoromethyl alkenes.
Topics & Concepts
Hydrogen atomAtom (system on chip)ChemistryHydrogen bondVisible spectrumHydrogenCrystallographyPhysicsStereochemistryPhotochemistryMoleculeGroup (periodic table)Organic chemistryOpticsComputer scienceEmbedded systemFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods