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Issue 45, 2019
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Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: scope and mechanism

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Abstract

A series of molybdenum pincer complexes has been shown for the first time to be active in the catalytic hydrogenation of amides. Among the tested catalysts, Mo-1a proved to be particularly well suited for the selective C–N hydrogenolysis of N-methylated formanilides. Notably, high chemoselectivity was observed in the presence of certain reducible groups including even other amides. The general catalytic performance as well as selectivity issues could be rationalized taking an anionic Mo(0) as the active species. The interplay between the amide C[double bond, length as m-dash]O reduction and the catalyst poisoning by primary amides accounts for the selective hydrogenation of N-methylated formanilides. The catalyst resting state was found to be a Mo–alkoxo complex formed by reaction with the alcohol product. This species plays two opposed roles – it facilitates the protolytic cleavage of the C–N bond but it encumbers the activation of hydrogen.

Graphical abstract: Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: scope and mechanism

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Supplementary files

Article information


Submitted
12 Jul 2019
Accepted
21 Sep 2019
First published
08 Oct 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 10566-10576
Article type
Edge Article

Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: scope and mechanism

T. Leischner, L. Artús Suarez, A. Spannenberg, K. Junge, A. Nova and M. Beller, Chem. Sci., 2019, 10, 10566
DOI: 10.1039/C9SC03453F

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