Photoredox Activation of Organozinc Reagents: Barbier-Type Reaction of Alkyl Halides with α-(Trifluoromethyl)styrenes
Anton A. Gladkov, Grigory N. Chernov, Vitalij V. Levin, Vladimir A. Kokorekin, Alexander D. Dilman
Abstract
Organozinc reagents may be activated under blue light irradiation using an organic photocatalyst to generate alkyl radicals. The radicals are trapped by α-(trifluoromethyl)styrenes leading to gem-difluorinated products after elimination of fluoride. The reaction can be conveniently performed under Barbier conditions starting from organic iodides and bromides and elemental zinc.
Topics & Concepts
ChemistryTrifluoromethylReagentAlkylRadicalHalideZincPhotocatalysisFluorideOrganic chemistryPhotochemistryInorganic chemistryCatalysisRadical Photochemical ReactionsFluorine in Organic ChemistryOxidative Organic Chemistry Reactions