Electrochemical Synthesis of Polysubstituted Oxazoles from Ketones and Acetonitrile
Liang Bao, Chen Liu, Wenyi Li, Jiage Yu, Min Wang, Yunfei Zhang
Abstract
Herein we report an electrochemical strategy for the construction of polysubstituted oxazoles from easily available ketones and acetonitrile under room temperature. The method shows high efficiency, a broad substrate scope, and requires no external chemical oxidant. Mechanistic investigations suggest that the reaction proceeds through a Ritter-type reaction/oxidative cyclization using acetonitrile as the reactant and solvent. X-ray crystallographic analysis reveals that the reaction involves the attack of acetonitrile on the carbonyl carbon instead of the α-carbon.
Topics & Concepts
AcetonitrileChemistryElectrochemistrySolventSubstrate (aquarium)Combinatorial chemistryOrganic chemistryCarbon fibersPhotochemistryPhysical chemistryElectrodeComposite numberGeologyOceanographyMaterials scienceComposite materialOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions