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Electrochemical Oxidative Cleavage of Alkynes to Carboxylic Acids.

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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… Click to show full 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.

Keywords: alkynes carboxylic; carboxylic acids; cleavage alkynes; oxidative cleavage; electrochemical oxidative

Journal Title: Organic letters
Year Published: 2023

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