Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes

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...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (19), p.7804-7808
Main Authors: Iosub, Andrei V, Moravčík, Štefan, Wallentin, Carl-Johan, Bergman, Joakim
Format: Article
Language:English
Subjects:
alkyl-halides
anhydrides
base
Chemistry
direct conversion
direct hydrogenation
discovery
hydride
hydrosilylation
ketones
mild
Organic Chemistry
Organisk kemi
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02779