Activation of Anthraquinone’s Electrophilicity by Light for a Dynamic C–O Bond

Авторы: Bykov Vasily N., Ukhanev Stepan A., Ushakov Igor A., Vologzhanina Anna V., Antsiferov Evgenii A., Klimenko Lyubov S., Lvov Andrey G.
Журнал: Journal of the American Chemical Society
Год издания: 2024
Издательство: American Chemical Society
Местоположение издательства: United States
DOI: 10.1021/jacs.3c12461
Аннотация: Coupling of photoswitching with dynamic covalent chemistry enables control of the formation and cleavage of covalent bonds by light irradiation. peri-Aryloxyanthraquinones feature an exclusive ability to switch electrophilicity by interconversion between para- and ana-quinone isomers, which was used for the first time for the implementation of a dynamic C–O bond. Photogenerated ana-isomers undergo a concerted oxa-Michael addition of phenols to give hitherto unknown 4-hydroxy-10,10-diaryloxyanthracen-9-ones. These species were found to be in equilibrium with the corresponding ana-quinones, thus forming a dynamic covalent system of a new type. Withdrawal of the colored ana-quinones from the equilibria by visible light irradiation resulted in two para-quinones with “locked” aryloxy groups.
Добавил в систему: Вологжанина Анна Владимировна

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