|
ИСТИНА |
Войти в систему Регистрация |
ИСТИНА ИНХС РАН |
||
Picket-fence ruthenium(II) phthalocyaninates bearing (1R,2S,5R)-menthoxy groups as prototype of chiral catalystsстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 15 февраля 2024 г.
- Авторы: Kroitor Andrey P., Sinelshchikova Anna A., Grigoriev Mikhail S., Kirakosyan Gayane A., Martynov Alexander G., Gorbunova Yulia G., Sorokin Alexander B.
- Журнал: Dyes and Pigments
- Том: 222
- Год издания: 2024
- Издательство: Elsevier BV
- Местоположение издательства: Netherlands
- Номер статьи: 111830
- DOI: 10.1016/j.dyepig.2023.111830
- Аннотация: We report design and synthesis of novel picket-fence phthalocyanines to access the ruthenium(II) complexes carrying di-(1R,2S,5R)-menthoxy substituted aryloxy-groups. Owing to bulkiness of such groups located either at peripheral (β) or non-peripheral (α) positions, they are nearly orthogonal to the plane of the phthalocyanine thus creating a chiral environment around the metal center. This orthogonality was supported by X-ray analysis of corresponding phthalonitrile precursors (86.0◦ and 81.4◦ angles between the planes of aromatic moieties for α- and β-substituted phthalonitriles, respectively). As a proof of concept, the synthesized complexes were investi- gated as catalysts in a benchmark reaction of the cyclopropanation of styrene by ethyl diazoacetate. While the β-substituted complex showed very low enantioselectivity, the α-substituted analogue afforded a moderate asymmetric induction towards ethyl (1S,2R)-2-phenylcyclopropane-1-carboxylate. This result emphasizes the importance of appropriate arrangement of the chiral groups relative to the phthalocyanine catalytic center and provides guidelines for further elaboration of phthalocyanine catalysts for asymmetric transfer of carbenes.
- Добавил в систему: Мартынов Александр Германович