Electrochemical synthesis of sulfinic and sulfonic esters from sulfonyl hydrazides

Abstract

An electrochemical synthetic method for the synthesis of sulfinic esters and sulfonic esters from sulfonyl hydrazides was developed. Alkyl sulfinic esters were synthesized by treating sulfonyl hydrazides with trialkyl orthoformate in a DMF solvent at a constant current of 5 mA and then optimizing the reaction conditions. Conversely, alkyl sulfonic esters were exclusively obtained when the reaction was conducted in alkyl alcohol solvents at a constant current of 15 mA. The various substituted arylsulfonyl hydrazides afforded moderate to good yields of the desired sulfinic esters and sulfonic esters. Mechanistic investigations revealed that sulfonyl radicals were formed through electrochemical oxidation and that they react with alkyl radicals or alkoxy radicals to generate the respective ester products.