Electrochemical Decarboxylative Oxygenation of Carboxylic Acids
Xiangtai Meng, Hehua Xu, Yu Zheng, Jinyue Luo, Shenlin Huang
Abstract
A straightforward electrosynthesis of carbonyls from aliphatic carboxylic acids has been developed through electrochemical decarboxylative oxygenation. This newly developed transformation features metal free, ubiquitous substrates, good functional group tolerance, and mild conditions. Diverse primary, secondary, as well as tertiary carboxylic acids were amenable to this sequence, furnishing valuable ketones, aldehydes, and amides in good to excellent yields. Moreover, preliminary mechanistic studies indicate that the electrochemically generated carbocation is trapped with water and followed by TEMPO-mediated electrocatalytic oxidation of the alcohol intermediate.
Topics & Concepts
ElectrosynthesisCarbocationElectrochemistryChemistryCarboxylic acidPrimary (astronomy)Alcohol oxidationDecarboxylationAlcoholOrganic chemistryFunctional groupCombinatorial chemistryCatalysisElectrodePolymerPhysicsAstronomyPhysical chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions