Radical Substitution of Polyfluoroarenes and Heteroarenes Promoted by Photoredox Activation of Organozinc Iodides
Anton A. Gladkov, Vitalij V. Levin, Alexander D. Dilman
Abstract
Abstract Aromatic compounds interact with organozinc reagents under photoredox conditions, leading to the substitution products. The reaction is performed under blue light irradiation via in situ generated organozinc reagents (Barbier conditions), which are oxidized by the photocatalyst, followed by radical attack at the aromatic substrate. The method works with polyfluorinated arenes, 2‐chlorobenzoxazoles, and 2‐sulfonyl‐substituted benzothiazole.
Topics & Concepts
ChemistryBenzothiazoleReagentSulfonylElectrophilic aromatic substitutionPhotoredox catalysisCombinatorial chemistryPhotochemistrySubstitution reactionSubstrate (aquarium)PhotocatalysisOrganic chemistryCatalysisAlkylGeologyOceanographyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesOxidative Organic Chemistry Reactions