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Synthesis of methyl β-alkylcarboxylates by Pd/diphosphine-catalyzed methoxycarbonylation of methylenealkanes RCH2CH2C(R)=CH2статья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 14 августа 2019 г.
- Авторы: Nifant’ev Ilya E., Sevostyanova Nadezhda T., Batashev Sergey A., Vinogradov Alexey A., Vinogradov Alexander A., Churakov Andrei V., Ivchenko Pavel V.
- Журнал: Applied Catalysis A: General
- Том: 581
- Год издания: 2019
- Издательство: Elsevier BV
- Местоположение издательства: Netherlands
- Первая страница: 123
- Последняя страница: 132
- DOI: 10.1016/j.apcata.2019.05.030
- Аннотация: A series of methylenealkanes RCH2CH2(R)C=CH2 (R = n-butyl, n-hexyl, isopropyl and isobutyl), which are products of selective zirconocene-catalyzed dimerization of α-olefins, were introduced into Pd-catalyzed methoxycarbonylation. With the use of 5-methyleneundecane (1-hexene dimer) as a substrate, the roles of protic acid, Lewis acid and molecular hydrogen were established for model Pd(II)/PPh3 and Pd(II)/diphosphine catalysts. A series of bridged diphosphines were studied as catalyst components L in PdCl2/L-catalyzed methoxycarbonylation in the presence of H2. One of the nine diphosphines studied, trans-2,3-bis(diphenylphosphinomethyl)norbornane, demonstrated the best catalytic results in terms of catalytic activity, selectivity and isolated yields of the products. Under the optimized conditions during 24 h experiments, dimers RCH2CH2(R)C=CH2 were transformed to methyl carboxylates RCH2CH2(R)CHCH2COOMe with 99+% regioselectivity; isolated yields were 62–81%. In that way, the catalytic methoxycarbonylation of synthetically available methylenealkanes is an effective approach to branched carboxylic acids, with high prospects for practical application.
- Добавил в систему: Ивченко Павел Васильевич