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Issue 21, 2018
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Efficient nickel-catalysed N-alkylation of amines with alcohols

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Abstract

The selective N-alkylation of amines with alcohols via the borrowing hydrogen strategy represents a prominent sustainable catalytic method, which produces water as the only by-product and is ideally suited for the catalytic transformation of widely available alcohol reaction partners that can be derived from renewable resources. Intensive research has been devoted to the development of novel catalysts that are mainly based on expensive noble metals. However, the availability of homogeneous or heterogeneous non-precious metal catalysts for this transformation is very limited. Herein we present a highly active and remarkably easy-to-prepare Ni based catalyst system for the selective N-alkylation of amines with alcohols, that is in situ generated from Ni(COD)2 and KOH under ligand-free conditions. This novel method is very efficient for the functionalization of aniline and derivatives with a wide range of aromatic and aliphatic alcohols as well as diols and exhibits excellent functional group tolerance including halides, benzodioxane and heteroaromatic groups. Several TEM measurements combined with elemental analysis were conducted in order to gain insight into the nature of the active catalyst and factors influencing reactivity.

Graphical abstract: Efficient nickel-catalysed N-alkylation of amines with alcohols

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Supplementary files

Article information


Submitted
08 Jun 2018
Accepted
11 Sep 2018
First published
03 Oct 2018

Catal. Sci. Technol., 2018,8, 5498-5505
Article type
Paper

Efficient nickel-catalysed N-alkylation of amines with alcohols

A. Afanasenko, S. Elangovan, M. C. A. Stuart, G. Bonura, F. Frusteri and K. Barta, Catal. Sci. Technol., 2018, 8, 5498
DOI: 10.1039/C8CY01200H

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