Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds

Daniel Scott; Matthew J. Fuchter; Andrew Ashley

doi:10.1021/ja5088979

Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds

Daniel Scott, Matthew J. Fuchter, Andrew Ashley

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

117 Citations (SciVal)

Abstract

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.

Original language	English
Pages (from-to)	15813–15816
Journal	Journal of the American Chemical Society
Volume	136
Issue number	45
DOIs	https://doi.org/10.1021/ja5088979
Publication status	Published - 21 Oct 2014

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10.1021/ja5088979Licence: CC BY

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title = "Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds",

abstract = "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 Br{\o}nsted base yet moderately strong donor, plays a pivotal role.",

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AU - Fuchter, Matthew J.

AU - Ashley, Andrew

PY - 2014/10/21

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N2 - 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.

AB - 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.

U2 - 10.1021/ja5088979

DO - 10.1021/ja5088979

M3 - Article

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SP - 15813

EP - 15816

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 45

ER -

Nonmetal Catalyzed Hydrogenation of Carbonyl Compounds

Abstract

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