E. V. Verbitskiy, E. M. Dinastiya, O. S. Eltsov, E. F. Zhilina, A. V. Shchepochkin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, “Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties”, Mendeleev Commun., 2020, том 30, выпуск 2,страницы 142

Эта публикация цитируется в 12 статьях

Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties

E. V. Verbitskiy^ab, E. M. Dinastiya^a, O. S. Eltsov^ab, E. F. Zhilina^a, A. V. Shchepochkin^ab, G. L. Rusinov^ab, O. N. Chupakhin^ab, V. N. Charushin^ab

^a I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation

Аннотация: Di(het)areno[e,l][1,3]diazapyrene core was constructed by FeCl3-mediated intramolecular oxidative cyclodehydrogenation of 5-[2,6-di(het)arylphenyl]pyrimidine precursors, which in turn were obtained by the Suzuki cross-coupling of 5-(2,6-dibromophenyl)pyrimidine derivative with the corresponding (het)arylboronic acids. Molecular orbital calculations as well as redox and photophysical measurements show that the fused products are promising for organic electronic application.

Ключевые слова: pyrimidines, pyrenes, azapyrenes, C–H functionalization, Suzuki reaction, bromination, annulation, iron trichloride.

Язык публикации: английский

DOI: 10.1016/j.mencom.2020.03.003