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Synthesis 2009(9): 1463-1468  
DOI: 10.1055/s-0028-1088164
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Matthias Mentela, Matthias J. Beiera, Rolf Breinbauer*a,b
a Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany
b Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, 8010 Graz, Austria
Fax: +43(316)8738740; e-Mail: breinbauer@tugraz.at;
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Publikationsverlauf

Received 23 October 2008
Publikationsdatum:
25. März 2009 (online)

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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.

Key words

electroorganic synthesis - hydrazides - reduction - tin - amides

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