Electrochemical Oxidative Cleavage of Alkynes to Carboxylic Acids
Qingyuan Feng, Yamin Wang, Binnan Zheng, Shenlin Huang
Abstract
A sustainable method for converting terminal alkynes into their corresponding carboxylic acids is reported using synthetic electrolysis in an undivided cell at room temperature. This protocol, avoiding transition metal catalysis and stoichiometric chemical oxidants, tolerates a variety of aryl, heteroaryl, and alkyl akynes. Preliminary mechanistic studies demonstrate that sodium nitrite serves a triple role as the electrolyte, nitryl radical precursor, and a nitrosating reagent.
Topics & Concepts
ChemistryReagentElectrolysisArylCatalysisElectrochemistryCombinatorial chemistryAlkylStoichiometryElectrolyteOrganic chemistryElectrodePhysical chemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesOxidative Organic Chemistry Reactions