Synthesis 2018; 50(21): 4290-4294
DOI: 10.1055/s-0037-1610069
paper
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient NHC-Catalyzed Aerobic Oxidation of Aldehydes to Carboxylic Acids

Anil Kumar Khatana
a  Division of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow-226014, India   Email: btiwari@cbmr.res.in
b  Department of Chemistry, Central University of Haryana, Mahendergarh-123031, Haryana, India
,
Vikram Singh
a  Division of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow-226014, India   Email: btiwari@cbmr.res.in
,
Manoj Kumar Gupta
b  Department of Chemistry, Central University of Haryana, Mahendergarh-123031, Haryana, India
,
a  Division of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow-226014, India   Email: btiwari@cbmr.res.in
› Author Affiliations
B.T. thanks the Science & Engineering Research Board (SERB), New Delhi, India, for a research grant (EMR/2015/00097).
Further Information

Publication History

Received: 31 March 2018

Accepted after revision: 27 April 2018

Publication Date:
16 July 2018 (eFirst)

These authors contributed equally to this work.

Dedicated to Dr. Srivari Chandrasekhar, IICT, Hyderabad, India on his 54th birthday

Published as part of the Special Topic Heterocycles as Catalysts, Ligands, and Targets

Abstract

An N-heterocyclic carbene (NHC) organocatalytic aerobic oxidation of aldehydes to the corresponding carboxylic acids is explored. Remarkably, this method allows for efficient conversion of different classes of aldehydes including highly challenging electron-rich aryl aldehydes, ortho-substituted aryl aldehydes, various heteroaromatic aldehydes and α,β-unsaturated aldehydes under mild reaction conditions. These substrates, under previously reported NHC-catalyzed methods, are typically unreactive or give poor yields, require high reaction temperatures and reaction times of several days.

Supporting Information

 
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