Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds

Solutions of the Lewis acid B­(C6F5)3 in 1,4-dioxane are found to effectively catalyze the hydrogenation of a variety of ketones and aldehydes. These reactions, the first to allow entirely metal-free catalytic hydrogenation of carbonyl groups under relatively mild reaction conditions, are found to p...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-11, Vol.136 (45), p.15813-15816
Main Authors: Scott, Daniel J, Fuchter, Matthew J, Ashley, Andrew E
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Catalysis
Dioxanes - chemistry
Hydrogenation
Ketones - chemistry
Lewis Acids - chemistry
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Summary:Solutions of the Lewis acid B­(C6F5)3 in 1,4-dioxane are found to effectively catalyze the hydrogenation of a variety of ketones and aldehydes. These reactions, the first to allow entirely metal-free catalytic hydrogenation of carbonyl groups under relatively mild reaction conditions, are found to proceed via a “frustrated Lewis pair” mechanism in which the solvent, a weak Brønsted base yet moderately strong donor, plays a pivotal role.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja5088979