Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration

Three series of poly(ionic) carbosilane dendrimers peripherally functionalized with imidazolium groups substituted on N-3 with methyl, isopropyl and 2,6-diisopropylphenyl (Dipp) were prepared up to the 3rd generation together with model monovalent imidazolium iodides and used as N-heterocyclic carbe...

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Autores principales:	Alena Krupková, Klára Kubátová, Lucie Červenková Šťastná, Petra Cuřínová, Monika Müllerová, Jindřich Karban, Jan Čermák, Tomáš Strašák
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	immobilization organocatalysis N-heterocyclic carbenes umpolung poly(cationic) dendrimers nanofiltration Chemical technology TP1-1185 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/72162f35f7004cc1ade5afba5c9b2fb2
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spelling	oai:doaj.org-article:72162f35f7004cc1ade5afba5c9b2fb22021-11-25T17:05:47ZPoly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration10.3390/catal111113172073-4344https://doaj.org/article/72162f35f7004cc1ade5afba5c9b2fb22021-10-01T00:00:00Zhttps://www.mdpi.com/2073-4344/11/11/1317https://doaj.org/toc/2073-4344Three series of poly(ionic) carbosilane dendrimers peripherally functionalized with imidazolium groups substituted on N-3 with methyl, isopropyl and 2,6-diisopropylphenyl (Dipp) were prepared up to the 3rd generation together with model monovalent imidazolium iodides and used as N-heterocyclic carbene (NHC) precursors. Catalytic activity of model and dendritic NHCs generated in situ by deprotonation with DBU was tested in redox esterification of α,β-unsaturated aldehydes and the influence of substitution, dendrimer generation, temperature and substrate structure on the reaction outcome was evaluated. Dipp substituted NHCs showed high activity and selectivity in the reaction with primary alcohols. Effectiveness of organic solvent nanofiltration for the recycling of dendritic NHCs was demonstrated on the 1st generation Dipp substituted catalyst in model redox esterification of cinnamaldehyde with benzyl alcohol. A marked increase in both activity and selectivity in the first four reaction runs was observed and this improved performance was preserved in the following catalytic cycles.Alena KrupkováKlára KubátováLucie Červenková ŠťastnáPetra CuřínováMonika MüllerováJindřich KarbanJan ČermákTomáš StrašákMDPI AGarticleimmobilizationorganocatalysisN-heterocyclic carbenesumpolungpoly(cationic) dendrimersnanofiltrationChemical technologyTP1-1185ChemistryQD1-999ENCatalysts, Vol 11, Iss 1317, p 1317 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	immobilization organocatalysis N-heterocyclic carbenes umpolung poly(cationic) dendrimers nanofiltration Chemical technology TP1-1185 Chemistry QD1-999
spellingShingle	immobilization organocatalysis N-heterocyclic carbenes umpolung poly(cationic) dendrimers nanofiltration Chemical technology TP1-1185 Chemistry QD1-999 Alena Krupková Klára Kubátová Lucie Červenková Šťastná Petra Cuřínová Monika Müllerová Jindřich Karban Jan Čermák Tomáš Strašák Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration
description	Three series of poly(ionic) carbosilane dendrimers peripherally functionalized with imidazolium groups substituted on N-3 with methyl, isopropyl and 2,6-diisopropylphenyl (Dipp) were prepared up to the 3rd generation together with model monovalent imidazolium iodides and used as N-heterocyclic carbene (NHC) precursors. Catalytic activity of model and dendritic NHCs generated in situ by deprotonation with DBU was tested in redox esterification of α,β-unsaturated aldehydes and the influence of substitution, dendrimer generation, temperature and substrate structure on the reaction outcome was evaluated. Dipp substituted NHCs showed high activity and selectivity in the reaction with primary alcohols. Effectiveness of organic solvent nanofiltration for the recycling of dendritic NHCs was demonstrated on the 1st generation Dipp substituted catalyst in model redox esterification of cinnamaldehyde with benzyl alcohol. A marked increase in both activity and selectivity in the first four reaction runs was observed and this improved performance was preserved in the following catalytic cycles.
format	article
author	Alena Krupková Klára Kubátová Lucie Červenková Šťastná Petra Cuřínová Monika Müllerová Jindřich Karban Jan Čermák Tomáš Strašák
author_facet	Alena Krupková Klára Kubátová Lucie Červenková Šťastná Petra Cuřínová Monika Müllerová Jindřich Karban Jan Čermák Tomáš Strašák
author_sort	Alena Krupková
title	Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration
title_short	Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration
title_full	Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration
title_fullStr	Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration
title_full_unstemmed	Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration
title_sort	poly(imidazolium) carbosilane dendrimers: synthesis, catalytic activity in redox esterification of α,β-unsaturated aldehydes and recycling via organic solvent nanofiltration
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/72162f35f7004cc1ade5afba5c9b2fb2
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Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration

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