Issue 5, 2016

Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines

Abstract

A broad range of secondary and tertiary amides has been hydrogenated to the corresponding amines under mild conditions using an in situ catalyst generated by combining [Ru(acac)3], 1,1,1-tris(diphenylphosphinomethyl)ethane (Triphos) and Yb(OTf)3. The presence of the metal triflate allows to mitigate reaction conditions compared to previous reports thus improving yields and selectivities in the desired amines. The excellent isolated yields of two scale-up experiments corroborate the feasibility of the reaction protocol. Control experiments indicate that, after the initial reduction of the amide carbonyl group, the reaction proceeds through the reductive amination of the alcohol with the amine arising from collapse of the intermediate hemiaminal.

Graphical abstract: Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Dec 2015
Accepted
08 Feb 2016
First published
09 Feb 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 3432-3442

Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines

J. R. Cabrero-Antonino, E. Alberico, K. Junge, H. Junge and M. Beller, Chem. Sci., 2016, 7, 3432 DOI: 10.1039/C5SC04671H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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