Electrochemical Oxidative Cleavage of Alkynes to Carboxylic Acids

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.

Automated summary

A sustainable method for converting terminal alkynes into carboxylic acids is developed using synthetic electrolysis in an undivided cell at room temperature. This protocol, which eliminates the need for transition metal catalysis and stoichiometric chemical oxidants, is compatible with various aryl, heteroaryl, and alkyl alkynes. Mechanistic studies suggest that sodium nitrite plays a triple role as an electrolyte, nitryl radical precursor, and nitrosating reagent.