Clays catalyzed cascade Prins and Prins-Friedel-Crafts reactions for synthesis of terpenoid-derived polycyclic compounds

Clays catalyzed cascade Prins and Prins-Friedel-Crafts reactions for synthesis of terpenoid-derived polycyclic compounds Full article

Journal

Applied Catalysis A: General
ISSN: 0926-860X , E-ISSN: 1873-3875

Output data

Year: 2022, Volume: 629, Article number : 118395, Pages count : DOI: 10.1016/j.apcata.2021.118395

Tags

Cascade reactions; Clays; Prins/Friedel-Crafts; Terpenoids, Polycyclic compounds

Authors

Sidorenko A.Y. ¹ , Kurban Y.M. ¹ , Kravtsova A.V. ¹ , Il'ina I.V. ² , Li-Zhulanov N.S. ² , Korchagina D.V. ² , Sánchez-Velandia J.E. ³ , Aho A. ⁴ , Volcho K.P. ² , Salakhutdinov N.F. ² , Murzin D.Y. ⁴ , Agabekov V.E. ¹

Affiliations

1	Institute of Chemistry of New Materials of National Academy of Sciences of Belarus, Skaryna str, 36, Minsk, 220141, Belarus
2	Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, Novosibirsk, 630090, Russian Federation
3	Centro de Investigaciones en Catálisis, Universidad Industrial de Santander, Escuela de Química, km.2. vía El Refugio, Piedecuesta, Santander 680006, Colombia
4	Åbo Akademi University, Biskopsgatan 8, Turku/Åbo, 20500, Finland

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 Brønsted 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. © 2021 Elsevier B.V.

Sidorenko A.Y. , Kurban Y.M. , Kravtsova A.V. , Il'ina I.V. , Li-Zhulanov N.S. , Korchagina D.V. , Sánchez-Velandia J.E. , Aho A. , Volcho K.P. , Salakhutdinov N.F. , Murzin D.Y. , Agabekov V.E.
Clays catalyzed cascade Prins and Prins-Friedel-Crafts reactions for synthesis of terpenoid-derived polycyclic compounds
Applied Catalysis A: General. 2022. V.629. 118395 . DOI: 10.1016/j.apcata.2021.118395 WOS Scopus РИНЦ

Published print:

Jan 5, 2022

Web of science	WOS:000724337100004
Scopus	2-s2.0-85118981105
Elibrary	47525994
OpenAlex	W3205688045