Preprint Communication Version 1 Preserved in Portico This version is not peer-reviewed

Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines.

Cheng Chen
ORCID logo ,
Yang Miao
,
Kimmy De Winter
,
Hua-Jing Wang
,
Patrick Demeyere
,
Ye Yuan
* ,
Francis Verpoort
* ORCID logo
Version 1 : Received: 29 August 2018 / Approved: 29 August 2018 / Online: 29 August 2018 (11:48:42 CEST)

A peer-reviewed article of this Preprint also exists.

Chen, C.; Miao, Y.; De Winter, K.; Wang, H.-J.; Demeyere, P.; Yuan, Y.; Verpoort, F. Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines. Molecules 2018, 23, 2413. Chen, C.; Miao, Y.; De Winter, K.; Wang, H.-J.; Demeyere, P.; Yuan, Y.; Verpoort, F. Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines. Molecules 2018, 23, 2413.

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 HR-MS analyses revealed that two tetra-carbene complexes were probably generated from the in situ catalytic system.

Keywords

ruthenium (Ru); N-heterocyclic carbenes (NHCs); homogeneous catalysis; in situ; amide bonds; synthesis.

Subject

Chemistry and Materials Science, Organic Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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