Heterogeneous palladium-based catalyst promoted reduction of oximes to amines: using H2 at 1 atm in H2O under mild conditions

Yaxu Liu; Ziyi Quan; Shaopo He; Zexi Zhao; Jiang Wang; Bo Wang

doi:10.1039/C9RE00003H

Heterogeneous palladium-based catalyst promoted reduction of oximes to amines: using H₂ at 1 atm in H₂O under mild conditions†

Yaxu Liu,^a Ziyi Quan,^a Shaopo He,^a Zexi Zhao,^a Jiang Wang*^a and Bo Wang

*^abc

Author affiliations

* Corresponding authors

^a Key Laboratory of Advanced Materials of Tropical Island Resources (Hainan University), Ministry of Education, Hainan University, No.58 Renmin AVE., Haikou 570228, P.R. China
E-mail: wangbo@hainanu.edu.cn, bo.wang@biotech.kth.se, wangjiang@hainanu.edu.cn

^b State Key Lab of Marine Resource Utilizations in South China Sea, Hainan University, No.58 Renmin AVE., Haikou 570228, P.R. China

^c Institute of Chemical Engineering, College of Materials and Chemical Engineering, Hainan University, No.58 Renmin AVE., Haikou 570228, P.R. China

Abstract

A highly active palladium-based heterogeneous catalyst with excellent activity for the hydrogenation of oximes to form amines was prepared from the metal precursor K₂PdCl₄ and 4-nitrobenzene-1,2-diamine. It is particularly suitable for the hydrogenation of oximes to prepare a wide spectrum of primary amines employing H₂ (1 atm) in H₂O under mild conditions. In addition, the heterogeneous catalyst can be easily recycled, and repeatedly reused for ten times without losing its catalytic activity and selectivity. This palladium-based catalyst and its developed procedures are applicable for both aliphatic and aromatic aldoximes and ketoximes. The corresponding primary amines could be afforded with good to excellent yields of up to >99%, representing the first examples proceeding in H₂O using 1 atm H₂ at rt and it is believed to possess great potential for sustainable industrial applications.

This article is part of the themed collection: 2019 Reaction Engineering in China

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Article information

DOI: https://doi.org/10.1039/C9RE00003H
Article type: Paper
Submitted: 02 Jan 2019
Accepted: 22 Mar 2019
First published: 22 Mar 2019

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React. Chem. Eng., 2019,4, 1145-1152

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Heterogeneous palladium-based catalyst promoted reduction of oximes to amines: using H₂ at 1 atm in H₂O under mild conditions

Y. Liu, Z. Quan, S. He, Z. Zhao, J. Wang and B. Wang, React. Chem. Eng., 2019, 4, 1145 DOI: 10.1039/C9RE00003H

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Reaction Chemistry & Engineering