Dehydroxylative Arylation of Alcohols via Paired Electrolysis
Zhihui Wang, Xiaoqian Zhao, Hongyu Wang, Li Xiuyun, Zhimin Xu, Velayudham Ramadoss, Lifang Tian, Yahui Wang
Abstract
Nonactivated alcohols along with arene compounds are used in electrochemical dehydroxylative arylation for constructing C(sp3)–C(sp2) bonds. The PIII reagent undergoes single-electron anodic oxidation to form its radical cation, which reacts with the alcohol to produce an alkoxytriphenylphosphine radical. Through spontaneous β-scission of the phosphoranyl radical, the C–O bond is cleaved to form an alkyl radical species, which couples with the radical anion generated by cathodic reduction of the electron-poor arene to afford the dehydroxylative arylated product.
Topics & Concepts
ChemistryReagentElectrolysisElectrochemistryRadical ionBond cleavageCathodic protectionMedicinal chemistryAlkylPhotochemistryAlcoholAnodic oxidationIonCombinatorial chemistryOrganic chemistryCatalysisElectrodeElectrolytePhysical chemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods