Electrochemical Direct α-Arylation of Alkylamines with Sulfonylarenes
Kyohei Yonekura, Mari Murooka, Kohei Aoki, Eiji Shirakawa
Abstract
The electrochemical α-arylation of alkylamines with sulfonylarenes has been developed. Here, diverse trialkylamines and aryl(dimethyl)amines are applicable to the α-arylation with sulfonylarenes having an azole, azine, and benzene nucleus. The α-arylation was scaled up using an electrolysis flow cell. Mechanistic studies show that anodic oxidation of an alkylamine with a sulfinate as a mediator followed by deprotonation gives an α-aminoalkyl radical, which undergoes homolytic aromatic substitution (HAS) on a sulfonylarene to give the corresponding α-arylalkylamine.
Topics & Concepts
ChemistryHomolysisDeprotonationElectrolysisElectrochemistryBenzeneAzineArylBulk electrolysisCombinatorial chemistryOrganic chemistryMedicinal chemistryRadicalCyclic voltammetryElectrodeElectrolytePhysical chemistryAlkylIonRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods