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Metal-Free Cross-Dehydrogenative C–O Coupling of Carbonyl Compounds with N-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperatureстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 20 мая 2020 г.
- Авторы: Крылов И.Б., Лопатьева Е.Р., Будников А.С., Никишин Г.И., Терентьев А.О.
- Журнал: Journal of Organic Chemistry
- Том: 85
- Номер: 4
- Год издания: 2020
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 1935
- Последняя страница: 1937
- DOI: 10.1021/acs.joc.9b02656
- Аннотация: Cross-dehydrogenative C–O coupling of N-hydroxyimides with ketones, esters, and carboxylic acids was achieved employing the di-tert-butyl peroxide as a source of free radicals and a dehydrogenating agent. The proposed method is experimentally simple and demonstrates the outstanding efficiency for the challenging CH substrates, such as unactivated esters and carboxylic acids. It was shown that N-hydroxyphthalimide drastically affects the oxidative properties of t-BuOOt-Bu by intercepting the t-BuO• radicals with the formation of phthalimide-N-oxyl radicals, a species responsible for both hydrogen atom abstraction from the CH reagent and the selective formation of the C–O coupling product by selective radical cross-recombination. The practical applicability of the developed method was exemplified by the single-stage synthesis of commercial reagent (known as Baran aminating reagent precursor) from isobutyric acid and N-hydroxysuccinimide, whereas in the standard synthetic approach, four stages are necessary.
- Добавил в систему: Будников Александр Сергеевич