Аннотация:
A highly regioselective reaction of pentafluoroacetanilide hydrodefluorination, which proceeds under the action of zinc in the presence of nickel complexes, leading to the formation of 2,3,4,5-tetra- and 3,4,5-trifluoroacetanilide was observed.
Ключевые слова:
Nickel, C-F bond activation, catalysis, fluoroanilines.
Тип публикации:
Статья
Язык публикации: английский
Образец цитирования:
S. A. Prikhod'ko, N. Yu. Adonin, D. E. Babushkin, V. N. Parmon, “Highly regioselective nickel-catalyzed hydrodefluorination of pentafluoroacetanilide”, Mendeleev Commun., 18:4 (2008), 211–212
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc3301
https://www.mathnet.ru/rus/mendc/v18/i4/p211
Эта публикация цитируется в следующих 25 статьяx:
S.A. Prikhod'ko, A Yu. Shabalin, N Yu Adonin, “New catalytic systems with chemically fixed nickel complexes in the reactions of reductive activation of C-F bonds in ionic liquid media”, Journal of Organometallic Chemistry, 950 (2021), 121995
C. Sloby, Catalysis from A to Z, 2020
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
S.A. Prikhod'ko, A.G. Popov, N.Yu. Adonin, “Effects arising from the replacement of aprotic dipolar solvents with ionic liquids in the nickel-catalyzed reduction of aryl chlorides”, Molecular Catalysis, 461 (2018), 19
L.Yu. Gurskaya, V.D. Shteingarts, “Ortho-hydrodefluorination of polyfluorinated 4-acetamidobiphenyls and synthesis of polyfluorinated 6-phenylquinolines”, Journal of Fluorine Chemistry, 156 (2013), 214
Moritz F. Kuehnel, Dieter Lentz, Thomas Braun, “Synthese fluorierter Bausteine durch Übergangsmetall‐vermittelte Hydrodefluorierungsreaktionen”, Angewandte Chemie, 125:12 (2013), 3412
Moritz F. Kuehnel, Dieter Lentz, Thomas Braun, “Synthesis of Fluorinated Building Blocks by Transition‐Metal‐Mediated Hydrodefluorination Reactions”, Angew Chem Int Ed, 52:12 (2013), 3328
S. A. Prikhod'kv, N. Yu. Adonin, V. N. Parmon, “Activation of C-F bonds in ionic liquids catalyzed by nickel complex compounds”, Russ Chem Bull, 62:1 (2013), 33
Juan Xiao, Jingjing Wu, Wenwen Zhao, Song Cao, “NiCl2(PCy3)2-catalyzed hydrodefluorination of fluoroarenes with LiAl(O-t-Bu)3H”, Journal of Fluorine Chemistry, 146 (2013), 76
Moritz F. Kuehnel, Philipp Holstein, Meike Kliche, Juliane Krüger, Stefan Matthies, Dominik Nitsch, Joseph Schutt, Michael Sparenberg, Dieter Lentz, “Titanium‐Catalyzed Vinylic and Allylic CF Bond Activation—Scope, Limitations and Mechanistic Insight”, Chemistry A European J, 18:34 (2012), 10701
David Breyer, Thomas Braun, Paul Kläring, “Synthesis and Reactivity of the Fluoro Complex trans-[Pd(F)(4-C5NF4)(iPr2PCH2CH2OCH3)2]: C–F Bond Formation and Catalytic C–F Bond Activation Reactions”, Organometallics, 31:4 (2012), 1417
Thomas R. Dugan, Jonathan M. Goldberg, William W. Brennessel, Patrick L. Holland, “Low-Coordinate Cobalt Fluoride Complexes: Synthesis, Reactions, and Production from C–F Activation Reactions”, Organometallics, 31:4 (2012), 1349
Peter Fischer, Kathrin Götz, Antonius Eichhorn, Udo Radius, “Decisive Steps of the Hydrodefluorination of Fluoroaromatics using [Ni(NHC)2]”, Organometallics, 31:4 (2012), 1374
Lauren Keyes, Alex D. Sun, Jennifer A. Love, “Exploration of the Scope of Pt‐Catalyzed C–F Activation”, Eur J Org Chem, 2011:20-21 (2011), 3985
Jingjing Wu, Song Cao, “Nickel‐Catalyzed Hydrodefluorination of Fluoroarenes and Trifluorotoluenes with Superhydride (Lithium Triethylborohydride)”, ChemCatChem, 3:10 (2011), 1582
Jing-Jing Wu, Jian-Hang Cheng, Jian Zhang, Li Shen, Xu-Hong Qian, Song Cao, “Non-catalytic conversion of C–F bonds of gem-difluoromethylene derivatives to C–H bonds with lithium aluminum hydride under room temperature”, Tetrahedron, 67:2 (2011), 285
Thomas Braun, Falk Wehmeier, “C–F Bond Activation of Highly Fluorinated Molecules at Rhodium: From Model Reactions to Catalysis”, Eur J Inorg Chem, 2011:5 (2011), 613
David Breyer, Thomas Braun, Anna Penner, “Isolation and reactivity of palladium hydrido complexes: intermediates in the hydrodefluorination of pentafluoropyridine”, Dalton Trans., 39:32 (2010), 7513
Sergey A. Prikhod'ko, Nicolay Yu. Adonin, Valentin N. Parmon, “The ionic liquid [bmim]Br as an alternative medium for the catalytic cleavage of aromatic C–F and C–Cl bonds”, Tetrahedron Letters, 51:17 (2010), 2265
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