Next Article in Journal
Synthesis and Characterization of Poly(Vinyl Alcohol)-Chitosan-Hydroxyapatite Scaffolds: A Promising Alternative for Bone Tissue Regeneration
Next Article in Special Issue
Density Functional Studies on Secondary Amides: Role of Steric Factors in Cis/Trans Isomerization
Previous Article in Journal / Special Issue
Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes
Open AccessCommunication

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

1
State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, China
2
School of Materials Science and Engineering, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, China
3
Odisee/KU Leuven Technology Campus, Gebroeders de Smetstraat 1, 9000 Ghent, Belgium
4
School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, China
5
National Research Tomsk Polytechnic University, Lenin Avenue 30, Tomsk 634050, Russian
6
Ghent University Global Campus, 119 Songdomunhwa-Ro, Yeonsu-Gu, Incheon 21985, Korea
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(10), 2413; https://doi.org/10.3390/molecules23102413
Received: 29 August 2018 / Revised: 17 September 2018 / Accepted: 18 September 2018 / Published: 20 September 2018
(This article belongs to the Special Issue Amide Bond Activation)
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. View Full-Text
Keywords: ruthenium (Ru); N-heterocyclic carbenes (NHCs); homogeneous catalysis; in situ; amide bonds; synthesis ruthenium (Ru); N-heterocyclic carbenes (NHCs); homogeneous catalysis; in situ; amide bonds; synthesis
Show Figures

Graphical abstract

MDPI and ACS Style

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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop