The Influence of Various N-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 N-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...

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Autores principales: Pieczykolan, Michał, Czaban-Jóźwiak, Justyna, Malinska, Maura, Woźniak, Krzysztof, Dorta, Reto, Rybicka, Anna, Kajetanowicz, Anna, Grela, Karol
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7287594/
https://www.ncbi.nlm.nih.gov/pubmed/32408688
http://dx.doi.org/10.3390/molecules25102282
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author Pieczykolan, Michał
Czaban-Jóźwiak, Justyna
Malinska, Maura
Woźniak, Krzysztof
Dorta, Reto
Rybicka, Anna
Kajetanowicz, Anna
Grela, Karol
author_facet Pieczykolan, Michał
Czaban-Jóźwiak, Justyna
Malinska, Maura
Woźniak, Krzysztof
Dorta, Reto
Rybicka, Anna
Kajetanowicz, Anna
Grela, Karol
author_sort Pieczykolan, Michał
collection PubMed
description A set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified N-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 (4a and 4b) 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 (4d–e) 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.
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spelling pubmed-72875942020-06-15 The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts Pieczykolan, Michał Czaban-Jóźwiak, Justyna Malinska, Maura Woźniak, Krzysztof Dorta, Reto Rybicka, Anna Kajetanowicz, Anna Grela, Karol Molecules Article A set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified N-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 (4a and 4b) 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 (4d–e) 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. MDPI 2020-05-12 /pmc/articles/PMC7287594/ /pubmed/32408688 http://dx.doi.org/10.3390/molecules25102282 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Pieczykolan, Michał
Czaban-Jóźwiak, Justyna
Malinska, Maura
Woźniak, Krzysztof
Dorta, Reto
Rybicka, Anna
Kajetanowicz, Anna
Grela, Karol
The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts
title The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts
title_full The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts
title_fullStr The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts
title_full_unstemmed The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts
title_short The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts
title_sort influence of various n-heterocyclic carbene ligands on activity of nitro-activated olefin metathesis catalysts
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7287594/
https://www.ncbi.nlm.nih.gov/pubmed/32408688
http://dx.doi.org/10.3390/molecules25102282
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