Mild and selective hydrogenation of aromatic and aliphatic (di)nitriles with a well-defined iron pincer complex

Christoph Bornschein, Svenja Werkmeister, Bianca Wendt, Haijun Jiao, Elisabetta Alberico, Wolfgang Baumann, Henrik Junge, Kathrin Junge and Matthias Beller ()
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Christoph Bornschein: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Svenja Werkmeister: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Bianca Wendt: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Haijun Jiao: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Elisabetta Alberico: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Wolfgang Baumann: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Henrik Junge: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Kathrin Junge: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Matthias Beller: Leibniz-Institut für Katalyse e.V. an der Universität Rostock

Nature Communications, 2014, vol. 5, issue 1, 1-11

Abstract: Abstract The catalytic hydrogenation of carboxylic acid derivatives represents an atom-efficient and clean reduction methodology in organic chemistry. More specifically, the selective hydrogenation of nitriles offers the possibility for a green synthesis of valuable primary amines. So far, this transformation lacks of useful, broadly applicable non-noble metal-based catalyst systems. In the present study, we describe a molecular-defined iron complex, which allows for the hydrogenation of aryl, alkyl, heterocyclic nitriles and dinitriles. By using an iron PNP pincer complex, we achieve very good functional group tolerance. Ester, ether, acetamido as well as amino substituents are not reduced in the presence of nitriles. Moreover, nitriles including an α,β-unsaturated double bond and halogenated derivatives are well tolerated in this reaction. Notably, our complex constitutes the first example of an homogeneous catalyst, which permits the selective hydrogenation of industrially important adipodinitrile to 1,6-hexamethylenediamine.

Date: 2014
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DOI: 10.1038/ncomms5111

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