The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4: H -imidazole N -oxide series

Yury A. Ten, Oleg G. Salnikov, Svetlana A. Amitina, Dmitri V. Stass, Tatyana V. Rybalova, Maxim S. Kazantsev, Artem S. Bogomyakov, Evgeny A. Mostovich, Dmitrii G. Mazhukin

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

3 Цитирования (Scopus)

Аннотация

2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-(4-iodophenyl)-4,4-dimethyl-4H-imidazole 3-oxide reacts with phenylboronic acid and its substituted derivatives in a cross-coupling reaction of the Suzuki-Miyaura type to form 5-biphenyl derivatives of 4H-imidazole-N-oxide. Interaction of the same compound with B2(pin)2 in the presence of PdCl2(PPh3)2 proceeds through the formation of intermediate 1,3,2-dioxoborolane and leads to the product of homocoupling: biphenyl-bis(imidazole). Oxidation of the resultant imidazoles with lead dioxide quantitatively yields stable conjugated phenoxyl-nitroxyl mono- and diradicals, which are of interest as electroactive paramagnetic materials. The crystal structure of the monoradical, 2,6-di-tert-butyl-4-[1-oxido-4-(biphenyl-4-yl)-5,5-dimethyl-1H-imidazole-2(5H)-ylidene]cyclohex-2,5-dienone, its magnetic susceptibility, EPR spectra of the obtained hybrid radicals in solution, and cyclic voltammetry characteristics of 4H-imidazoles were studied.

Язык оригиналаанглийский
Страницы (с-по)26099-26107
Число страниц9
ЖурналRSC Advances
Том8
Номер выпуска46
DOI
СостояниеОпубликовано - 1 янв 2018

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