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Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes

Journal article
Authors A. V. Iosub
S. Moravcik
Carl Johan Wallentin
J. Bergman
Published in Organic Letters
Volume 21
Issue 19
Pages 7804-7808
ISSN 1523-7060
Publication year 2019
Published at Department of Chemistry and Molecular Biology
Pages 7804-7808
Language en
Links dx.doi.org/10.1021/acs.orglett.9b02...
Keywords direct hydrogenation, direct conversion, alkyl-halides, hydrosilylation, hydride, ketones, anhydrides, base, mild, discovery, Chemistry
Subject categories Organic Chemistry

Abstract

The direct reduction of carboxylic acids to aldehydes is a fundamental transformation in organic synthesis. The combination of an air-stable Ni precatalyst, dimethyl dicarbonate as an activator, and silane reductant effects this reduction for a wide variety of substrates, including pharmaceutically relevant structures, in good yields and with no overreduction to alcohols. Moreover, this methodology is scalable, allows access to deuterated aldehydes, and is also compatible with one-pot utilization of the aldehyde products.

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