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

Loading...
Thumbnail Image
Date
2016
Volume
7
Issue
5
Journal
Chemical science
Series Titel
Book Title
Publisher
Cambridge : RSC
Link to publishers version
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.

Description
Keywords
Collections
License
CC BY 3.0 Unported