Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt−CuFe/Fe3O4 Catalyst and Ammonia Borane as Hydrogen Donor

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First Author:Rongxiu Guo

Correspondence Author:Hong-bin Sun, Dr. Dun Niu, Dr. Qionglin Liang

Co author:GuangQi He, Lei Liu, Yongjian Ai, Ze-nan Hu, Xinyue Zhang, Haimeng Tian

Journal:ChemPlusChem

Issue:8

Volume:85

Impact Factor:3.0

DOI number:10.1002/cplu.202000028

Affiliation of Author(s):Department of Chemistry, Northeastern University

Teaching and Research Group:物理化学

Place of Publication:GERMANY

Abstract:Abstract Hydrogenation of nitriles is an efficient and environmentally friendly route to synthesize symmetrical secondary amines, but it usually produces a mixture of amines, imines, and hydrogenolysis by-products. Herein we report a magnetic quaternary-component Pt−CuFe/Fe3O4 nanocatalyst system for the selective synthesis of symmetrical secondary amines with ammonia borane as hydrogen donor. The catalyst with a low Pt loading (0.456 wt%) is the source of the activity, and the d-band electron transfer from Cu to Fe enhances the selectivity. This synergistic effect results in the transformation of benzonitrile to dibenzylamine with excellent conversion (up to 99 %) and nearly quantitative selectivity (up to 96 %) under mild reaction conditions, nevertheless, the reaction TOF is as high as up to 1409.9 h−1. A variety of nitriles are suitable for the synthesis of symmetrical secondary amines. More importantly, unwanted hydrogenolysis byproducts, especially toluene, is not detected at all. In addition, the catalyst is magnetically recoverable, and it can be reused up to five times.

Key Words:amines,heterogeneous catalysis, hydrogen transfer, iron oxide, transition metals

Document Code:WOS:000563997000021

Discipline:Natural Science

First-Level Discipline:Chemistry

Page Number:1783-1788

ISSN No.:2192-6506

Translation or Not:no