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Organofluorine Chemistry: Promising Growth Areas and Challenges Обзор

Общая информация Язык: Английский, Жанр: Обзор (Review),
Статус опубликования: Опубликована, Оригинальность: Переводная
Журнал Russian Chemical Reviews
ISSN: 0036-021X , E-ISSN: 1468-4837
Вых. Данные Год: 2019, Том: 88, Номер: 5, Страницы: 425-569 Страниц : 145 DOI: 10.1070/RCR4871
Ключевые слова fluorine-containing heterocycles; biologically-active amides; one-pot synthesis; cross-coupling reaction; beta-aryl enamines; containing 2-arylhydrazono-1,3-dicarbonyl compounds; palladium-catalyzed difluoromethylation; direct nucleophilic difluoromethylation; polyfluoroorganoboron-oxygen compounds; copper-mediated difluoromethylation
Авторы Politanskaya Larisa V. 1 , Selivanova Galina A. 1 , Panteleeva Elena V. 1,2 , Tretyakov Evgeny V. 1,2 , Platonov Vyacheslav E. 1 , Nikul'shin Pavel V. 1 , Vinogradov Andrey S. 1 , Zonov Yaroslav V. 1 , Karpov Victor M. 1 , Mezhenkova Tatyana V. 1 , Vasilyev Aleksander V. 3,4 , Koldobskii Andrei B. 5 , Shilova Olga S. 5 , Morozova Sofia M. 5 , Burgart Yanina V. 6,7 , Shchegolkov Evgeny V. 6,7 , Saloutin Victor I. 6,7 , Sokolov Vladimir B. 8 , Aksinenko Aleksey Yu. 8 , Nenajdenko Valentine G. 9 , Moskalik Mikhail Yu. 10 , Astakhova Vera V. 10 , Shainyan Bagrat A. 10 , Tabolin Andrey A. 11 , Ioffe Sema L. 11 , Muzalevskiy Vasiliy M. 9 , Balenkova Elizaveta S. 9 , Shastin Alexey V. 12 , Tyutyunov Andrey A. 5 , Boiko Vladimir E. 5 , Igumnov Sergei M. 5 , Dilman Alexander D. 11 , Adonin Nicolay Yu. 13 , Bardin Vadim V. 1 , Masoud Salekh M. 5 , Vorobyeva Daria V. 5 , Osipov Sergey N. 5 , Nosova Emiliya V. 6,7 , Lipunova Galina N. 6,7 , Charushin Valery N. 6,7 , Prima Darya O. 1,14 , Makarov Arkady G. 1 , Zibarev Andrey V. 1,14 , Trofimov Boris A. 10 , Sobenina Lyubov N. 10 , Belyaeva Kseniya V. 10 , Sosnovskikh Vyacheslav Ya. 7 , Obydennov Dmitrii L. 7 , Usachev Sergey A. 7
Организации
1 N.N.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, prosp. Akademika Lavrentieva 9, 630090 Novosibirsk, Russian Federation
2 Novosibirsk State University, ul. Pirogova 2, 630090 Novosibirsk, Russian Federation
3 Saint Petersburg State Forest Technical University, Institutsky per. 5, 194021 Saint Petersburg, Russian Federation
4 Saint Petersburg State University, Universitetskaya nab. 7 – 9, 199034 Saint Petersburg, Russian Federation
5 A.N.Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, 119991 Moscow, Russian Federation
6 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, ul. S.Kovalevskoi 22/ul. Akademicheskaya 20, 620990 Ekaterinburg, Russian Federation
7 Ural Federal University named after the first President of Russia B.N.Yeltsin, ul. Mira 19, 620002 Ekaterinburg, Russian Federation
8 Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severnyi pr. 1, 142432 Chernogolovka, Moscow Region, Russian Federation
9 Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, stroenie 3, 119992 Moscow, Russian Federation
10 A.E.Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, ul. Favorskogo 1, 664033 Irkutsk, Russian Federation
11 N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
12 Institute of Problems of Chemical Physics, Russian Academy of Sciences, prosp. Akademika Semenova 1, 142432 Chernogolovka, Moscow Region, Russian Federation
13 Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, prosp. Akademika Lavrentieva 5, 630090 Novosibirsk, Russian Federation
14 Department of Chemistry, National Research University — Tomsk State University, prosp. Lenina 36, 634050 Tomsk, Russian Federation

Реферат: Currently, the chemistry of organofluorine compounds is a leading and rapidly developing area of organic chemistry. Fluorine present in a molecule largely determines its specific chemical and biological properties. This thematic issue covers the trends of organofluorine chemistry that have been actively developed in Russia the last 15 – 20 years. The review describes nucleophilic substitution and heterocyclization reactions involving fluorinated arenes and quinones and skeletal cationoid rearrangements in the polyfluoroarene series. The transformations involving CF3-substituted carbocations and radical cations are considered. Heterocyclization and oxidative addition reactions of trifluoroacetamide derivatives and transformations of the organic moiety in polyfluorinated organoboranes and borates with retention of the carbon – boron bond are discussed. Particular attention is devoted to catalytic olefination using freons as an efficient synthetic route to fluorinated compounds. The application of unsymmetrical fluorine-containing N-heterocyclic carbene ligands as catalysts for olefin metathesis is demonstrated. A variety of classes of organofluorine compounds are considered, in particular, polyfluorinated arenes and 1,2-diaminobenzenes, 1-halo-2-trifluoroacetylacetylenes, α-fluoronitro compounds, fluorinated heterocycles, 2-hydrazinylidene-1,3-dicarbonyl derivatives, imines and silanes. The potential practical applications of organofluorine compounds in fundamental organic chemistry, materials science and biomedicine are outlined. The bibliography includes 1019 references.
Библиографическая ссылка: Politanskaya L.V. , Selivanova G.A. , Panteleeva E.V. , Tretyakov E.V. , Platonov V.E. , Nikul'shin P.V. , Vinogradov A.S. , Zonov Y.V. , Karpov V.M. , Mezhenkova T.V. , Vasilyev A.V. , Koldobskii A.B. , Shilova O.S. , Morozova S.M. , Burgart Y.V. , Shchegolkov E.V. , Saloutin V.I. , Sokolov V.B. , Aksinenko A.Y. , Nenajdenko V.G. , Moskalik M.Y. , Astakhova V.V. , Shainyan B.A. , Tabolin A.A. , Ioffe S.L. , Muzalevskiy V.M. , Balenkova E.S. , Shastin A.V. , Tyutyunov A.A. , Boiko V.E. , Igumnov S.M. , Dilman A.D. , Adonin N.Y. , Bardin V.V. , Masoud S.M. , Vorobyeva D.V. , Osipov S.N. , Nosova E.V. , Lipunova G.N. , Charushin V.N. , Prima D.O. , Makarov A.G. , Zibarev A.V. , Trofimov B.A. , Sobenina L.N. , Belyaeva K.V. , Sosnovskikh V.Y. , Obydennov D.L. , Usachev S.A.
Organofluorine Chemistry: Promising Growth Areas and Challenges
Russian Chemical Reviews. 2019. V.88. N5. P.425-569. DOI: 10.1070/RCR4871 WOS Scopus РИНЦ
Оригинальная версия: Политанская Л.В. , Селиванова Г.А. , Пантелеева Е.В. , Третьяков Е.В. , Платонов В.Е. , Никульшин П.В. , Виноградов А.С. , Зонов Я.В. , Карпов В.М. , Меженкова Т.В. , Васильев А.В. , Колдобский А.Б. , Шилова О.С. , Морозова С.М. , Бургарт Я.В. , Щегольков Е.В. , Салоутин В.И. , Соколов В.Б. , Аксиненко А.Ю. , Ненайденко В.Г. , Москалик М.Ю. , Астахова В.В. , Шаинян Б.А. , Таболин А.А. , Иоффе С.Л. , Музалевский В.М. , Баленкова Е.С. , Шастин А.В. , Тютюнов А.А. , Бойко В.Э. , Игумнов С.М. , Дильман А.Д. , Адонин Н.Ю. , Бардин В.В. , Масоуд С.М. , Воробьева Д.В. , Осипов С.Н. , Носова Э.В. , Липунова Г.Н. , Чарушин В.Н. , Прима Д.О. , Макаров А.Г. , Зибарев А.В. , Трофимов Б.А. , Собенина Л.Н. , Беляева К.В. , Сосновских В.Я. , Обыденнов Д.Л. , Усачев С.А.
Перспективные точки роста и вызовы фторорганической химии
Успехи химии. 2019. Т.88. №5. С.425-569. DOI: 10.1070/RCR4871?locatt = label:RUSSIAN РИНЦ
Даты:
Поступила в редакцию: 16 нояб. 2018 г.
Опубликована online: 30 апр. 2019 г.
Опубликована в печати: 1 мая 2019 г.
Идентификаторы:
Web of science WOS:000466355000002
Scopus 2-s2.0-85066251313
РИНЦ 41801075
Chemical Abstracts 2019:1509837
Альметрики: