The effect of the active site and substrate structure in preparation of substituted tetrahydropyrans via intramolecular cyclization

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F24%3A10473836" target="_blank" >RIV/00216208:11310/24:10473836 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=crVopSr1Ji" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=crVopSr1Ji</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.cattod.2023.114465" target="_blank" >10.1016/j.cattod.2023.114465</a>

Jazyk výsledku

angličtina

Název v původním jazyce

The effect of the active site and substrate structure in preparation of substituted tetrahydropyrans via intramolecular cyclization

Popis výsledku v původním jazyce

Substituted tetrahydropyrans (THPs) are important biologically active compounds and synthetic intermediates. Their prevalence and diverse applications make them desirable targets in synthetic organic chemistry. Current synthetic routes for THP synthesis involve homogeneous catalysts and usually multiple steps and the use of expensive heavy metal catalysts, which pose environmental concerns. Therefore, there is a need for alternative approaches that can enhance efficiency, eco-friendliness, and cost-effectiveness This study focuses on the acid-catalyzed synthesis of THPs through the intramolecular cyclization of substituted (E)-5-phenylpent-4-en-1- olsover zeolites as heterogeneous catalysts. The study particularly focused on investigating the influence of functional groups, as well as substrate size, on the reaction outcome. The results demonstrated that electron-donating groups enhance the conversion of the reactants and increase selectivity towards THPs, while electron-withdrawing groups have the opposite effect. Furthermore, the cyclization reaction also occurred on substrates containing different aromatic cycles. However, the conversion of a bulky substrate containing naph-thyl group decreased due to mass transfer limitations. The catalytic performance of different types of zeolites with diverse acid sites was also examined. Bronsted acidic zeolites such as Al-BEA and Ga-BEA exhibited promising catalytic performance and 94 % and 83 % selectivity towards THPs, respectively. In contrast, Lewis acidic zeolites such as Sn-BEA, Ti-BEA, and Zr-BEA showed conversions below 6.5 % and poor selectivity, showing that Bronsted acidic zeolites are more suitable for the cyclization reaction than Lewis acidic zeolites.

Název v anglickém jazyce

The effect of the active site and substrate structure in preparation of substituted tetrahydropyrans via intramolecular cyclization

Popis výsledku anglicky

Substituted tetrahydropyrans (THPs) are important biologically active compounds and synthetic intermediates. Their prevalence and diverse applications make them desirable targets in synthetic organic chemistry. Current synthetic routes for THP synthesis involve homogeneous catalysts and usually multiple steps and the use of expensive heavy metal catalysts, which pose environmental concerns. Therefore, there is a need for alternative approaches that can enhance efficiency, eco-friendliness, and cost-effectiveness This study focuses on the acid-catalyzed synthesis of THPs through the intramolecular cyclization of substituted (E)-5-phenylpent-4-en-1- olsover zeolites as heterogeneous catalysts. The study particularly focused on investigating the influence of functional groups, as well as substrate size, on the reaction outcome. The results demonstrated that electron-donating groups enhance the conversion of the reactants and increase selectivity towards THPs, while electron-withdrawing groups have the opposite effect. Furthermore, the cyclization reaction also occurred on substrates containing different aromatic cycles. However, the conversion of a bulky substrate containing naph-thyl group decreased due to mass transfer limitations. The catalytic performance of different types of zeolites with diverse acid sites was also examined. Bronsted acidic zeolites such as Al-BEA and Ga-BEA exhibited promising catalytic performance and 94 % and 83 % selectivity towards THPs, respectively. In contrast, Lewis acidic zeolites such as Sn-BEA, Ti-BEA, and Zr-BEA showed conversions below 6.5 % and poor selectivity, showing that Bronsted acidic zeolites are more suitable for the cyclization reaction than Lewis acidic zeolites.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/EF19_073%2F0016935" target="_blank" >EF19_073/0016935: Grantová schémata na UK</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

Catalysis Today

ISSN

0920-5861

e-ISSN

1873-4308

Svazek periodika

429

Číslo periodika v rámci svazku

March

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

114465

Kód UT WoS článku

001133367300001

EID výsledku v databázi Scopus

2-s2.0-85178418096