Synthesis of isobenzofuran derivatives from renewable 2-carene over halloysite nanotubes

A. Yu Sidorenko, A. V. Kravtsova, P. Mäki-Arvela, A. Aho, T. Sandberg, I. V. Il'ina, N. S. Li-Zhulanov, D. V. Korchagina, K. P. Volcho, N. F. Salakhutdinov, D. Yu Murzin, V. E. Agabekov

Результат исследования: Научные публикации в периодических изданияхстатья

1 Цитирования (Scopus)

Аннотация

Condensation of a terpene 2-carene with 4-methoxybenzaldehyde over a range of acid aluminosilicates including halloysite nanotubes (HNT) was studied for as a model for preparation of isobenzofuran derivatives with a pharmaceutical potential. The catalysts were characterized by FTIR with pyridine, UV by adsorption of 2-phenylethylamine from the aqueous phase, SEM, TEM and N2 physisorption. The largest selectivity to the desired product (ca. 70%) over halloysite nanotubes is associated with weak acidity of these catalysts (45 μmol/g), allowing avoiding side isomerization and condensation reactions. Moreover, the highest yield on air-dry HNT clearly indicates that weak Brønsted sites favored the reaction. On the contrary, over strong Brønsted and Lewis acids (Amberlyst-15, scandium triflate), the yield of isobenzofurans did not exceed 16% with formation of mainly 2-carene isomerization products. DFT calculations showed that interactions of the aldehyde with cyclopropane moiety of 2-carene giving isobenzofurans are more beneficial than an alternative direct attack of a proton, leading to side reactions. A possibility to reuse of HNT catalyst was confirmed. Overall, halloysite is a highly effective catalyst for production of isobenzofuran compounds based on 2-carene.

Язык оригиналаанглийский
Номер статьи110974
Число страниц8
ЖурналMolecular Catalysis
Том490
DOI
СостояниеОпубликовано - июл 2020

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