Ruthenium-based catalytic systems incorporating a labile cyclooctadiene ligand with N-heterocyclic carbene precursors for the atom-economic alcohol amidation using amines

Cheng Chen, Yang Miao, Kimmy De Winter, Hua Jing Wang, Patrick Demeyere, Ye Yuan, Francis Verpoort

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Transition-metal-catalyzed amide-bond formation from alcohols and amines is an atom-economic and eco-friendly route. Herein, we identified a highly active in situ N-heterocyclic carbene (NHC)/ruthenium (Ru) catalytic system for this amide synthesis. Various substrates, including sterically hindered ones, could be directly transformed into the corresponding amides with the catalyst loading as low as 0.25 mol.%. In this system, we replaced the p-cymene ligand of the Ru source with a relatively labile cyclooctadiene (cod) ligand so as to more efficiently obtain the corresponding poly-carbene Ru species. Expectedly, the weaker cod ligand could be more easily substituted with multiple mono-NHC ligands. Further high-resolution mass spectrometry (HRMS) analyses revealed that two tetra-carbene complexes were probably generated from the in situ catalytic system.

Original languageEnglish
Article number2413
JournalMolecules
Volume23
Issue number10
DOIs
Publication statusPublished - 20 Sep 2018

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Ruthenium
carbenes
ruthenium
Amines
economics
amines
alcohols
Alcohols
Economics
Amides
amides
Ligands
Atoms
ligands
atoms
Transition metals
Mass spectrometry
Mass Spectrometry
mass spectroscopy
Metals

Keywords

  • Amide bonds
  • Homogeneous catalysis
  • In situ
  • N-heterocyclic carbenes (NHCs)
  • Ruthenium (Ru)
  • Synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ruthenium-based catalytic systems incorporating a labile cyclooctadiene ligand with N-heterocyclic carbene precursors for the atom-economic alcohol amidation using amines. / Chen, Cheng; Miao, Yang; De Winter, Kimmy; Wang, Hua Jing; Demeyere, Patrick; Yuan, Ye; Verpoort, Francis.

In: Molecules, Vol. 23, No. 10, 2413, 20.09.2018.

Research output: Contribution to journalArticle

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AU - Yuan, Ye

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