Cation Radical-Accelerated Nucleophilic Aromatic Substitution for Amination of Alkoxyarenes
Nicholas J. Venditto, David A. Nicewicz
Abstract
Nucleophilic aromatic substitution (SNAr) is a common method for arene functionalization; however, reactions of this type are typically limited to electron-deficient aromatic halides. Herein, we describe a mild, metal-free, cation-radical accelerated nucleophilic aromatic substitution (CRA-SNAr) using a potent, highly oxidizing acridinium photoredox catalyst. Selective substitution of arene C–O bonds on a wide array of aryl ether substrates was shown with a variety of primary amine nucleophiles. Mechanistic evidence is also presented that supports the proposed CRA-SNAr pathway.
Topics & Concepts
Nucleophilic aromatic substitutionChemistryAminationRadical-nucleophilic aromatic substitutionNucleophilic substitutionNucleophileElectrophilic aromatic substitutionSubstitution reactionEtherCombinatorial chemistryArylOxidizing agentMedicinal chemistryAromaticityOrganic chemistryCatalysisPhotochemistryAlkylMoleculeCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions