Defluoroalkylation of <i>gem</i>-Difluoroalkenes with Alcohols via C–F/C–H Coupling
Congjian Xia, Hai Hu, Wengang Xu, Baokai Yang, Qi Shao, Mingbo Wu
Abstract
A feasible and effective method to synthesize α-fluoroalkenyl alcohols was reported. With the cooperation of photoredox and hydrogen atom transfer (HAT) processes, defluoroalkylations of gem -difluoroalkenes occurred smoothly with alcohols under visible-light irradiation. Notably, the protocols feature broad scopes, mild conditions, and validity for the late-stage functionalization of bioactive molecule derivatives. Mechanistic studies suggested that the reaction occurred through the radical coupling of the alkyl radical and the fluoroalkenyl radical.
Topics & Concepts
ChemistryHydrogen atomAlkylSurface modificationMoleculeCombinatorial chemistryCoupling (piping)Coupling reactionRadicalPhotochemistryOrganic chemistryCatalysisPhysical chemistryMechanical engineeringEngineeringFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods