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General and Scalable Approach to A2 B- and A2 BC-Type Porphyrin Phosphonate Diestersстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
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Web of Science
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 9 июня 2017 г.
- Авторы: Enakieva Yulia Yu, Michalak Julien, Abdulaeva Inna A., Volostnykh Marina V., Stern Christine, Guilard Roger, Bessmertnykh-Lemeune Alla G., Gorbunova Yulia G., Tsivadze Aslan Yu, Kadish Karl M.
- Журнал: European Journal of Organic Chemistry
- Том: 2016
- Номер: 28
- Год издания: 2016
- Издательство: John Wiley & Sons Ltd.
- Местоположение издательства: United Kingdom
- Первая страница: 4881
- Последняя страница: 4892
- DOI: 10.1002/ejoc.201600857
- Аннотация: A two-step reaction sequence for accessing meso-(dialkoxyphosphoryl) porphyrins from readily available trans-A(2)-type porphyrins was developed. This approach involves bromination and subsequent palladium-catalyzed phosphonylation. Optimal conditions for both steps were identified after exploration of various reaction parameters such as solvent, temperature and catalyst. A series of dialkoxyphosphoryl-substituted A2B-porphyrins Zn3(a-g) bearing electron-donating, electron-withdrawing or sterically bulky substituents at the meso-aryl groups were prepared in overall yields close to 40 %. These compounds, being air-stable and soluble in most organic solvents, are valuable synthetic intermediates because they can be readily transformed into functionalized trans-A(2)BC-type porphyrins through regioselective functionalization at the unsubstituted meso position of the macrocycle. Therefore, this approach offers considerable promise for application to the synthesis of trans-A(2)BC-type porphyrins, including water-soluble derivatives, push-pull chromophores and bis(porphyrin)s.
- Добавил в систему: Горбунова Юлия Германовна