Chemoselective Henry reaction catalyzed by electro-generated base

Chemoselective Henry reaction catalyzed by electro-generated base Chemoselective synthesis of 2-nitroalkanols catalyzed by electro-generated base (EGBs) in the presence of acetonitrile and lithium perchlorate has been studied by cyclic voltammetry and controlled potential electrolysis techniques. Cathodic reduction of nitromethane at platinum cathode produces organic anion which acts as EGBs and undergoes condensation with carbonyl group of substituted aldehydic substrate to produce 2-nitroalkanols in 75–85 % yields. The controlled nucleophilicity of EGBs in organic solvent during electrochemical reaction makes it chemoselective which is a unique feature of this work. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Chemoselective Henry reaction catalyzed by electro-generated base

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Publisher
Springer Journals
Copyright
Copyright © 2012 by Springer Science+Business Media B.V.
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-012-0695-6
Publisher site
See Article on Publisher Site

Abstract

Chemoselective synthesis of 2-nitroalkanols catalyzed by electro-generated base (EGBs) in the presence of acetonitrile and lithium perchlorate has been studied by cyclic voltammetry and controlled potential electrolysis techniques. Cathodic reduction of nitromethane at platinum cathode produces organic anion which acts as EGBs and undergoes condensation with carbonyl group of substituted aldehydic substrate to produce 2-nitroalkanols in 75–85 % yields. The controlled nucleophilicity of EGBs in organic solvent during electrochemical reaction makes it chemoselective which is a unique feature of this work.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jul 8, 2012

References

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