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

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

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

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 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.

Original languageEnglish
Article number118395
JournalApplied Catalysis A: General
Volume629
Early online date13 Oct 2021
DOIs
Publication statusPublished - 5 Jan 2022
MoE publication typeA1 Journal article-refereed

Keywords

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

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