The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts
A set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified <i>N</i>-hetero-cyclic carbene (NHC) ligands have been obtained, characterised and studied in a set of model metathesis reactions. It was found that catalysts bearing stan...
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| Format: | Article |
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MDPI AG
2020-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/10/2282 |
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| author | Michał Pieczykolan Justyna Czaban-Jóźwiak Maura Malinska Krzysztof Woźniak Reto Dorta Anna Rybicka Anna Kajetanowicz Karol Grela |
| author_facet | Michał Pieczykolan Justyna Czaban-Jóźwiak Maura Malinska Krzysztof Woźniak Reto Dorta Anna Rybicka Anna Kajetanowicz Karol Grela |
| author_sort | Michał Pieczykolan |
| collection | DOAJ |
| description | A set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified <i>N</i>-hetero-cyclic carbene (NHC) ligands have been obtained, characterised and studied in a set of model metathesis reactions. It was found that catalysts bearing standard SIMes and SIPr ligands (<b>4a</b> and <b>4b</b>) gave the best results in metathesis of substrates with more accessible C–C double bonds. At the same time, catalysts bearing engineered naphthyl-substituted NHC ligands (<b>4d</b>–<b>e</b>) exhibited high activity towards formation of tetrasubstituted C–C double bonds, the reaction which was traditionally Achilles’ heel of the nitro-activated Hoveyda–Grubbs catalyst. |
| first_indexed | 2024-03-10T19:52:09Z |
| format | Article |
| id | doaj.art-0fda7f5f2fb34a2f895f52856b1b6599 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:52:09Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0fda7f5f2fb34a2f895f52856b1b65992023-11-20T00:13:46ZengMDPI AGMolecules1420-30492020-05-012510228210.3390/molecules25102282The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis CatalystsMichał Pieczykolan0Justyna Czaban-Jóźwiak1Maura Malinska2Krzysztof Woźniak3Reto Dorta4Anna Rybicka5Anna Kajetanowicz6Karol Grela7Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandFaculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, PolandFaculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, PolandDepartment of Chemistry, School of Molecular Sciences, University of Western Australia, 35 Stirling Highway, Perth 6009, AustraliaFaculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, PolandFaculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, PolandInstitute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandA set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified <i>N</i>-hetero-cyclic carbene (NHC) ligands have been obtained, characterised and studied in a set of model metathesis reactions. It was found that catalysts bearing standard SIMes and SIPr ligands (<b>4a</b> and <b>4b</b>) gave the best results in metathesis of substrates with more accessible C–C double bonds. At the same time, catalysts bearing engineered naphthyl-substituted NHC ligands (<b>4d</b>–<b>e</b>) exhibited high activity towards formation of tetrasubstituted C–C double bonds, the reaction which was traditionally Achilles’ heel of the nitro-activated Hoveyda–Grubbs catalyst.https://www.mdpi.com/1420-3049/25/10/2282metathesisrutheniumnitro catalystsNHC ligandsolefins |
| spellingShingle | Michał Pieczykolan Justyna Czaban-Jóźwiak Maura Malinska Krzysztof Woźniak Reto Dorta Anna Rybicka Anna Kajetanowicz Karol Grela The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts Molecules metathesis ruthenium nitro catalysts NHC ligands olefins |
| title | The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts |
| title_full | The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts |
| title_fullStr | The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts |
| title_full_unstemmed | The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts |
| title_short | The Influence of Various <i>N</i>-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts |
| title_sort | influence of various i n i heterocyclic carbene ligands on activity of nitro activated olefin metathesis catalysts |
| topic | metathesis ruthenium nitro catalysts NHC ligands olefins |
| url | https://www.mdpi.com/1420-3049/25/10/2282 |
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