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Selective cross-dehydrogenative C-O coupling of N-hydroxy compounds with pyrazolones. Introduction of the diacetyliminoxyl radical into the practice of organic synthesisстатья
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: 17 октября 2017 г.
- Авторы: Krylov Igor B., Paveliev Stanislav A., Shelimov Boris N., Lokshin Boris V., Garbuzova Irina A., Tafeenko Viktor A., Chernyshev Vladimir V., Budnikov Alexander S., Nikishin Gennady I., Terent'ev Alexander O.
- Журнал: Organic Chemistry Frontiers
- Том: 4
- Номер: 10
- Год издания: 2017
- Первая страница: 1947
- Последняя страница: 1957
- DOI: 10.1039/c7qo00447h
- Аннотация: Oxidative C-O coupling of pyrazolones with N-hydroxy compounds of different classes (N-hydroxyphthalimide, N-hydroxybenzotriazole, oximes) was achieved; both one-electron oxidants (Fe(ClO4)(3), (NH4)(2)Ce(NO3)(6)) and two-electron oxidants (PhI(OAc)(2), Pb(OAc)(4)) are applicable, and the yields reach 91%. Apparently, the coupling proceeds via the formation of N-oxyl radicals from N-hydroxy compounds. One of the N-oxyl intermediates, the diacetyliminoxyl radical, was found to be exclusively stable in solution in spite of being sterically unhindered; it was isolated from an oxidant and used as a new reagent for the synthesis and mechanism study. The products of C-O coupling of pyrazolones with N-hydroxyphthalimide can be easily transformed into aminooxy compounds, valuable substances for combinatorial chemistry.
- Добавил в систему: Чернышев Владимир Васильевич