Efficient nickel-catalysed N-alkylation of amines with alcohols

Anastasiia Afanasenko, Saravanakumar Elangovan, Marc C. A. Stuart, Giuseppe Bonura, Francesco Frusteri, Katalin Barta*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

21 Citations (Scopus)
227 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)5498-5505
Number of pages8
JournalCatalysis Science & Technology
Volume8
Issue number21
DOIs
Publication statusPublished - 7-Nov-2018

Keywords

  • COMPLEX REDUCING AGENTS
  • REDUCTIVE AMINATION
  • HETEROGENEOUS CATALYSIS
  • NANOPARTICLES
  • HYDROAMINATION
  • ACTIVATION
  • ALDEHYDES
  • LIQUIDS
  • KETONES

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