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

Anil Kumar Khatana; Vikram Singh; Manoj Kumar Gupta; Bhoopendra Tiwari

doi:10.1055/s-0037-1610069

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(21): 4290-4294
DOI: 10.1055/s-0037-1610069

paper

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

Anil Kumar Khatana

^aDivision of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow-226014, India eMail: btiwari@cbmr.res.in

^bDepartment of Chemistry, Central University of Haryana, Mahendergarh-123031, Haryana, India

,

Vikram Singh

^aDivision of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow-226014, India eMail: btiwari@cbmr.res.in

,

Manoj Kumar Gupta

^bDepartment of Chemistry, Central University of Haryana, Mahendergarh-123031, Haryana, India

,

Bhoopendra Tiwari *

^aDivision of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow-226014, India eMail: btiwari@cbmr.res.in

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Abstract

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^‡ These authors contributed equally to this work.

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

Key words

carboxylic acids - aldehydes - N-heterocyclic carbenes - aerobic oxidation - organocatalysis

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