An Environmentally Benign Electrochemical Process for the Reduction of Carboxylic Acid Hydrazides to Amides

Abstract

The transformation of acid hydrazides to primary amides is of certain relevance for the organic synthesis of complex molecules. While existing methods require harsh reaction conditions, we present an electrochemical approach in which monoacylhydrazines are reduced to primary amides in 40-90% yield in a divided electrochemical cell with a tin cathode. This method proved superior to reduction by sodium/mercury or lithium/biphenyl in terms of yield and practicability. Most importantly, the new method is distinguished by its tolerance of aryl halogen and olefinic groups.