@article{1d988348cf2745e18f65a31a40146f1c,
title = "Clays catalyzed cascade Prins and Prins-Friedel-Crafts reactions for synthesis of terpenoid-derived polycyclic compounds",
abstract = "The Prins/Friedel-Crafts cascade reactions of the terpenoid trans-4-hydroxymethyl-2-carene (synthesized from 3-carene) with aromatic aldehydes were systematically studied for the first time on acidic mesoporous clays (halloysite, illite, montmorillonites). Both the reaction rate and selectivity to the desired polycyclic product with tetrahydrofuran moiety increased with an increase in the catalyst acidity and their drying temperature, indicating that relatively strong Br{\o}nsted and Lewis acid sites favored their formation. The best activity and selectivity (up to 97%) was demonstrated over commercial montmorillonite K-10 with acidity of ca. 100 μmol/g. In contrast, on strongest acids (resin Amberlyst-15), dehydration/aromatization of the substrate was observed. It was shown, that mesoporosity of the catalyst is one of the key factors governing catalytic behavior. The presence of at least one an electron-donor substituent at the meta-position of benzaldehyde is critical for the Prins-Friedel-Crafts reaction. Overall, available montmorillonites are an effective replacement for homogeneous catalysts for the Prins/Friedel-Crafts cascade reactions.",
keywords = "Cascade reactions, Clays, Prins/Friedel-Crafts, Terpenoids, Polycyclic compounds",
author = "Sidorenko, {A. Yu} and Kurban, {Yu M.} and Kravtsova, {A. V.} and Il'ina, {I. V.} and Li-Zhulanov, {N. S.} and Korchagina, {D. V.} and S{\'a}nchez-Velandia, {J. E.} and A. Aho and Volcho, {K. P.} and Salakhutdinov, {N. F.} and Murzin, {D. Yu} and Agabekov, {V. E.}",
note = "Funding Information: The research was financially supported by Belarusian Republican Foundation for Fundamental Research , Belarus (BRFFR, grant X20R-001 ) and Russian Foundation for Basic Research , Russia (RFBR, grant 20–53-00004 Bel_a ). The authors are grateful to Dr. T.F. Kuznetsova (IGICh of NAS of Belarus) for performing N 2 physisorption and to K. Dubatouka (IChNM of NAS of Belarus) for recording of EDX spectra. J.E. S{\'a}nchez-Velandia thanks to Pontificia Universidad Javeriana for providing computational powder. Funding Information: The research was financially supported by Belarusian Republican Foundation for Fundamental Research, Belarus (BRFFR, grant X20R-001) and Russian Foundation for Basic Research, Russia (RFBR, grant 20?53-00004 Bel_a). The authors are grateful to Dr. T.F. Kuznetsova (IGICh of NAS of Belarus) for performing N2 physisorption and to K. Dubatouka (IChNM of NAS of Belarus) for recording of EDX spectra. J.E. S?nchez-Velandia thanks to Pontificia Universidad Javeriana for providing computational powder. Publisher Copyright: {\textcopyright} 2021 Elsevier B.V.",
year = "2022",
month = jan,
day = "5",
doi = "10.1016/j.apcata.2021.118395",
language = "English",
volume = "629",
journal = "Applied Catalysis A: General",
issn = "0926-860X",
publisher = "Elsevier",
}