Electrosynthesis of 2-Substituted Benzoxazoles via Intramolecular Shono-Type Oxidative Coupling of Glycine Derivatives
Lei Liu, Zhenhui Xu, Tao Liu, Chao Xu, Wangqin Zhang, Xiangqi Hua, Fei Ling, Weihui Zhong
Abstract
Herein, an atom-economical and eco-friendly electrochemical oxidation/cyclization of glycine derivatives through intramolecular Shono-type oxidative coupling is disclosed, leading to a variety of 2-substituted benzoxazoles in 51–85% yields. This oxidative cyclization proceeded in transition metal- and oxidant-free conditions and generated H2 as only a byproduct. Additionally, gram-scale reactions and a broad substrate scope demonstrated the synthetic usefulness of this protocol.
Topics & Concepts
ChemistryIntramolecular forceElectrosynthesisOxidative coupling of methaneGlycineOxidative phosphorylationCombinatorial chemistrySubstrate (aquarium)StereochemistryElectrochemistryMedicinal chemistryOrganic chemistryCatalysisAmino acidBiochemistryOceanographyGeologyPhysical chemistryElectrodeCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques