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, Matthias Beller

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247 Scopus citations

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,Π2-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.

Original languageEnglish
Article number4111
JournalNature Communications
Volume5
DOIs
StatePublished - 27 Jun 2014
Externally publishedYes

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