Аннотация:
Cross-coupling of NH-pyrroles with 1-bromo-2-(trifluoroacetyl) acetylene in the Al2O3 medium affords (E)-4-bromo-1,1,1-trifluoro-4-(pyrrol-2-yl)but-3-en-2-ones instead of the expected 2-ethynylated products. Quantum-chemical analysis shows strong intramolecular hydrogen bonding between NH and trifluoroacetyl groups, higher NH acidity and deeper charge transfer to the ethenyl moiety, which determines the reaction pathway.
Образец цитирования:
D. N. Tomilin, D. Yu. Soshnikov, A. B. Trofimov, M. D. Gotsko, L. N. Sobenina, I. A. Ushakov, A. V. Afonin, A. B. Koldobskii, N. M. Vitkovskaya, B. A. Trofimov, “Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight”, Mendeleev Commun., 26:6 (2016), 480–482
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc2252
https://www.mathnet.ru/rus/mendc/v26/i6/p480
Эта публикация цитируется в следующих 11 статьяx:
L. N. Sobenina, E. F. Sagitova, O. V. Petrova, B. A. Trofimov, “Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry”, Mendeleev Commun., 31:5 (2021), 573–583
Lyubov' N. Sobenina, Boris A. Trofimov, “Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media”, Molecules, 25:11 (2020), 2490
Andrei V. Afonin, Alexander V. Vashchenko, “Benchmark calculations of intramolecular hydrogen bond energy based on molecular tailoring and function‐based approaches: Developing hybrid approach”, Int J of Quantum Chemistry, 119:21 (2019)
Denis N. Tomilin, Maxim D. Gotsko, Lyubov N. Sobenina, Igor A. Ushakov, Boris A. Trofimov, “A hydrogen pump: Transfer of four hydrogens from a cyclohexane ring to a triple bond during a menthofuran/bromoacetylene adduct rearrangement”, Tetrahedron Letters, 60:28 (2019), 1864
E. F. Sagitova, D. N. Tomilin, O. V. Petrova, A. B. Budaev, L. N. Sobenina, B. A. Trofimov, G. Q. Yang, R. Hu, “Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines”, Mendeleev Commun., 29:6 (2019), 658–660
Л. В. Политанская, Г. А. Селиванова, Е. В. Пантелеева, Е. В. Третьяков, В. Е. Платонов, П. В. Никульшин, А. С. Виноградов, Я. В. Зонов, В. М. Карпов, Т. В. Меженкова, А. В. Васильев, А. Б. Колдобский, О. С. Шилова, С. М. Морозова, Я. В. Бургарт, Е. В. Щегольков, В. И. Салоутин, В. Б. Соколов, А. Ю. Аксиненко, В. Г. Ненайденко, М. Ю. Москалик, В. В. Астахова, Б. А. Шаинян, А. А. Таболин, С. Л. Иоффе, В. М. Музалевский, Е. С. Баленкова, А. В. Шастин, А. А. Тютюнов, В. Э. Бойко, С. М. Игумнов, А. Д. Дильман, Н. Ю. Адонин, В. В. Бардин, С. М. Масоуд, Д. В. Воробьева, С. Н. Осипов, Э. В. Носова, Г. Н. Липунова, В. Н. Чарушин, Д. О. Прима, А. Г. Макаров, А. В. Зибарев, Б. А. Трофимов, Л. Н. Собенина, К. В. Беляева, В. Я. Сосновских, Д. Л. Обыденнов, С. А. Усачев, “Перспективные точки роста и вызовы фторорганической химии”, Усп. хим., 88:5 (2019), 425–569; L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul'shin, A. S. Vinogradov, Ya. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin, V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A. Usachev, “Organofluorine chemistry: promising growth areas and challenges”, Russian Chem. Reviews, 88:5 (2019), 425–569
Lyubov N. Sobenina, Denis N. Tomilin, Maxim D. Gotsko, Igor A. Ushakov, Boris A. Trofimov, “Transition metal-free cross-coupling of furan ring with haloacetylenes”, Tetrahedron, 74:13 (2018), 1565
Andrei V. Afonin, Irina V. Sterkhova, Alexander V. Vashchenko, Mark V. Sigalov, “Estimating the energy of intramolecular bifurcated (three-centered) hydrogen bond by X-ray, IR and 1 H NMR spectroscopy, and QTAIM calculations”, Journal of Molecular Structure, 1163 (2018), 185
M. A. Melkozerova, O. I. Gyrdasova, I. V. Baklanova, E. V. Vladimirova, E. V. Zabolotskaya, V. N. Krasil'nikov, “The effect of preparation method on the defect structure and luminescence properties of γ-Al2O3”, Mendeleev Commun., 28:6 (2018), 668–670
D. N. Tomilin, L. N. Sobenina, M. D. Gotsko, I. A. Ushakov, B. A. Trofimov, “Reaction of 1-(het)aryl-3-bromoprop-2-ynones with furans in solid metal oxides or salts: cross-coupling or cycloaddition?”, Mendeleev Commun., 28:1 (2018), 20–21
B. Trofimov, A. M. Belogolova, D. Yu. Soshnikov, T. E. Moskovskaya, N. M. Vitkovskaya, B. A. Trofimov, “Propagator quantum chemical study of S-cis-(Z)-2-(2-formylethenyl)pyrrole: electronic structure and aspects of intramolecular hydrogen bond manifestation in ionization spectra”, Russ Chem Bull, 66:12 (2017), 2241
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