Вид документа : Статья из журнала Шифр издания : 54/M 65 Автор(ы) : Verbitskiy E. V., Cheprakova E. M., Zhilina E. F., Kodess M. I., Ezhikova M. A., Pervova M. G., Slepukhin P. A., Charushin V. N., Chupakhin O. N. Заглавие : Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (SNH) in 5-bromopyrimidine by action of bithiophene and its analogues Место публикации : Tetrahedron. - 2013. - Vol.69, №25. - С. 5164-5172 ББК : 54 Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ Ключевые слова (''Своб.индексиров.''): c–h bond activations--pyrimidines--palladium Аннотация: 5-Bromopyrimidine reacts with 2,2′-bithiophene, [2,2′:5′,2″]terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl–aryl C–C coupling. However 5-bromo-4-(het)aryl-pyrimidines have been prepared from the same starting materials through the SNH-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas–liquid chromatography/mass-spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed Доп.точки доступа: Verbitskiy, E. V.; Cheprakova, E. M.; Zhilina, E. F.; Kodess, M. I.; Кодесс Михаил Исаакович; Ezhikova, M. A.; Pervova, M. G.; Slepukhin, P. A.; Charushin, V. N.; Chupakhin, O. N.