Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds | Zendy

Daniel J. Scott | Zendy; Matthew J. Fuchter | Zendy; Andrew E. Ashley | Zendy

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Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds

Author(s) -

Daniel J. Scott,

Matthew J. Fuchter,

Andrew E. Ashley

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja5088979

Subject(s) - chemistry , lewis acids and bases , catalysis , nonmetal , brønsted–lowry acid–base theory , frustrated lewis pair , solvent , organic chemistry , metal , medicinal chemistry

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.

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