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Nickel(ii) and nickel(0) complexes as precursors of nickel nanoparticles for the catalytic hydrogenation of benzonitrile

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Abstract

The use of the nickel(II) complex [(TEEDA)NiCl2] (1; TEEDA= N,N,N′,N′-tetraethyl-ethylendiamine) and nickel(0) complex [Ni(COD)2] (5) as pre-catalysts in the additive-free catalytic hydrogenation of benzonitrile (BN) is reported. In the presence of 1 (1 mol%), BN was hydrogenated under relatively mild reaction conditions (100 °C, 120 psi H2, 72 h) to the corresponding secondary imine, N-benzylidenebenzylamine (BBA), in very good yield (83%). As a counterpart, 5 (1 mol%) selectively hydrogenated BN to benzylamine (BA) in excellent yield (96%) under similar reaction conditions (80 °C, 120 psi H2, 24 h). In both cases, nickel nanoparticles (Ni-NPs) were identified as the catalytically active species. These Ni-NPs were formed in situ from 1 and 5 without external additives or additional stabilizers. The use of complex 5 was extended to the hydrogenation of different (hetero) aromatic and aliphatic nitriles.

Graphical abstract: Nickel(ii) and nickel(0) complexes as precursors of nickel nanoparticles for the catalytic hydrogenation of benzonitrile

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Article information


Submitted
17 Oct 2019
Accepted
12 Dec 2019
First published
13 Dec 2019

New J. Chem., 2020, Advance Article
Article type
Paper

Nickel(II) and nickel(0) complexes as precursors of nickel nanoparticles for the catalytic hydrogenation of benzonitrile

A. A. Rodríguez, J. A. Garduño and J. J. García, New J. Chem., 2020, Advance Article , DOI: 10.1039/C9NJ05221F

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