Synthesis 2021; 53(06): 1023-1034
DOI: 10.1055/s-0040-1706102
short review

Direct Oxidation of Primary Alcohols to Carboxylic Acids

,
T.J.W. and V.C. are sponsored by the US National Science Foundation (CHE-1856395) and the US Department of Energy, Office of Energy Efficiency and Renewable Energy (DE-EE-0008825).


Abstract

Oxidation of primary alcohols to carboxylic acids is a fundamental transformation in organic chemistry, yet despite its simplicity, extensive use, and relationship to pH, it remains a subject of active research for synthetic organic chemists. Since 2013, a great number of new methods have emerged that utilize transition-metal compounds as catalysts for acceptorless dehydrogenation of alcohols to carboxylates. The interest in this reaction is explained by its atom economy, which is in accord with the principles of sustainability and green chemistry. Therefore, the methods for the direct synthesis of carboxylic acids from alcohols is ripe for a modern survey, which we provide in this review.

1 Introduction

2 Thermodynamics of Primary Alcohol Oxidation

3 Oxometalate Oxidation

4 Transfer Dehydrogenation

5 Acceptorless Dehydrogenation

6 Electrochemical Methods

7 Outlook



Publication History

Received: 05 October 2020

Accepted after revision: 16 November 2020

Publication Date:
17 December 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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