Electrophotocatalytic C–H Functionalization of Ethers with High Regioselectivity
He Huang, Zack M. Strater, Tristan H. Lambert
Abstract
The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.
Topics & Concepts
ChemistryRegioselectivitySurface modificationDicationHydrogen atomPhotochemistrySubstrate (aquarium)ElectrochemistryRadical ionCatalysisCombinatorial chemistryIonOrganic chemistryAlkylOceanographyPhysical chemistryElectrodeGeologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions