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Issue 8, 2020
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Rational selection of co-catalysts for the deaminative hydrogenation of amides

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Abstract

The catalytic hydrogenation of amides is an atom economical method to synthesize amines. Previously, it was serendipitously discovered that the combination of a secondary amide co-catalyst with (iPrPNP)Fe(H)(CO) (iPrPNP = N[CH2CH2(PiPr2)]2), results in a highly active base metal system for deaminative amide hydrogenation. Here, we use DFT to develop an improved co-catalyst for amide hydrogenation. Initially, we computationally evaluated the ability of a series of co-catalysts to accelerate the turnover-limiting proton transfer during C–N bond cleavage and poison the (iPrPNP)Fe(H)(CO) catalyst through a side reaction. TBD (triazabicyclodecene) was identified as the leading co-catalyst. It was experimentally confirmed that when TBD is combined with (iPrPNP)Fe(H)(CO) a remarkably active system for amide hydrogenation is generated. TBD also enhances the activity of other catalysts for amide hydrogenation and our results provide guidelines for the rational design of future co-catalysts.

Graphical abstract: Rational selection of co-catalysts for the deaminative hydrogenation of amides

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Supplementary files

Article information


Submitted
25 Jul 2019
Accepted
17 Jan 2020
First published
20 Jan 2020

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

Chem. Sci., 2020,11, 2225-2230
Article type
Edge Article

Rational selection of co-catalysts for the deaminative hydrogenation of amides

L. Artús Suàrez, U. Jayarathne, D. Balcells, W. H. Bernskoetter, N. Hazari, M. Jaraiz and A. Nova, Chem. Sci., 2020, 11, 2225
DOI: 10.1039/C9SC03812D

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