Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines
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...
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MDPI AG
2018-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/10/2413 |
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| author | Cheng Chen Yang Miao Kimmy De Winter Hua-Jing Wang Patrick Demeyere Ye Yuan Francis Verpoort |
| author_facet | Cheng Chen Yang Miao Kimmy De Winter Hua-Jing Wang Patrick Demeyere Ye Yuan Francis Verpoort |
| author_sort | Cheng Chen |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-14T14:06:13Z |
| format | Article |
| id | doaj.art-3f152211569249bba7b8eec21c027afd |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-14T14:06:13Z |
| publishDate | 2018-09-01 |
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| series | Molecules |
| spelling | doaj.art-3f152211569249bba7b8eec21c027afd2022-12-21T22:58:30ZengMDPI AGMolecules1420-30492018-09-012310241310.3390/molecules23102413molecules23102413Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using AminesCheng Chen0Yang Miao1Kimmy De Winter2Hua-Jing Wang3Patrick Demeyere4Ye Yuan5Francis Verpoort6State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, ChinaSchool of Materials Science and Engineering, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, ChinaOdisee/KU Leuven Technology Campus, Gebroeders de Smetstraat 1, 9000 Ghent, BelgiumSchool of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, ChinaOdisee/KU Leuven Technology Campus, Gebroeders de Smetstraat 1, 9000 Ghent, BelgiumState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, ChinaState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, ChinaTransition-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.http://www.mdpi.com/1420-3049/23/10/2413ruthenium (Ru)N-heterocyclic carbenes (NHCs)homogeneous catalysisin situamide bondssynthesis |
| spellingShingle | Cheng Chen Yang Miao Kimmy De Winter Hua-Jing Wang Patrick Demeyere Ye Yuan Francis Verpoort Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines Molecules ruthenium (Ru) N-heterocyclic carbenes (NHCs) homogeneous catalysis in situ amide bonds synthesis |
| title | Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines |
| title_full | Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines |
| title_fullStr | Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines |
| title_full_unstemmed | Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines |
| title_short | Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines |
| title_sort | ruthenium based catalytic systems incorporating a labile cyclooctadiene ligand with n heterocyclic carbene precursors for the atom economic alcohol amidation using amines |
| topic | ruthenium (Ru) N-heterocyclic carbenes (NHCs) homogeneous catalysis in situ amide bonds synthesis |
| url | http://www.mdpi.com/1420-3049/23/10/2413 |
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