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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F21%3A00547595" target="_blank" >RIV/67985858:_____/21:00547595 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.mdpi.com/2073-4344/11/11/1317" target="_blank" >https://www.mdpi.com/2073-4344/11/11/1317</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/catal11111317" target="_blank" >10.3390/catal11111317</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Catalysts

ISSN

2073-4344

e-ISSN

2073-4344

Svazek periodika

11

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

17

Strana od-do

1317

Kód UT WoS článku

000724512100001

EID výsledku v databázi Scopus

2-s2.0-85118171504