The effect of the active site and substrate structure in preparation of substituted tetrahydropyrans via intramolecular cyclization
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
The effect of the active site and substrate structure in preparation of substituted tetrahydropyrans via intramolecular cyclization
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
<a href="/en/project/EF19_073%2F0016935" target="_blank" >EF19_073/0016935: Grant schemes at Charles University</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Catalysis Today
ISSN
0920-5861
e-ISSN
1873-4308
Volume of the periodical
429
Issue of the periodical within the volume
March
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
8
Pages from-to
114465
UT code for WoS article
001133367300001
EID of the result in the Scopus database
2-s2.0-85178418096