Organofluorine Chemistry: Promising Growth Areas and Challenges | Sciact - CRIS-system of Boreskov Institute of Catalysis

Organofluorine Chemistry: Promising Growth Areas and Challenges Review

Journal

Russian Chemical Reviews
ISSN: 0036-021X , E-ISSN: 1468-4837

Output data

Year: 2019, Volume: 88, Number: 5, Pages: 425-569 Pages count : 145 DOI: 10.1070/RCR4871

Tags

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

Authors

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

Affiliations

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

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.

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 AN OpenAlex

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

Submitted:	Nov 16, 2018
Published online:	Apr 30, 2019
Published print:	May 1, 2019

Web of science:	WOS:000466355000002
Scopus:	2-s2.0-85066251313
Elibrary:	41801075
Chemical Abstracts:	2019:1509837
OpenAlex:	W2799524300

DB	Citing
Web of science	142
Scopus	140
Elibrary	142
OpenAlex	133