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Usp. Khim., 2019, Volume 88, Issue 5, Pages 425–569 (Mi rcr4253)  

Organofluorine chemistry: promising growth areas and challenges

L. V. Politanskayaa, G. A. Selivanovaa, E. V. Panteleevaab, E. V. Tretyakovab, V. E. Platonova, P. V. Nikul'shina, A. S. Vinogradova, Ya. V. Zonova, V. M. Karpova, T. V. Mezhenkovaa, A. V. Vasilyevcd, A. B. Koldobskiie, O. S. Shilovae, S. M. Morozovae, Ya. V. Burgartfg, E. V. Shchegolkovfg, V. I. Saloutinfg, V. B. Sokolovh, A. Yu. Aksinenkoh, V. G. Nenajdenkoi, M. Yu. Moskalikj, V. V. Astakhovaj, B. A. Shainyanj, A. A. Tabolink, S. L. Ioffek, V. M. Muzalevskiyi, E. S. Balenkovai, A. V. Shastinl, A. A. Tyutyunove, V. E. Boikoe, S. M. Igumnove, A. D. Dilmank, N. Yu. Adoninm, V. V. Bardina, S. M. Masoude, D. V. Vorobyevae, S. N. Osipove, E. V. Nosovafg, G. N. Lipunovafg, V. N. Charushinfg, D. O. Primaan, A. G. Makarova, A. V. Zibarevan, B. A. Trofimovj, L. N. Sobeninaj, K. V. Belyaevaj, V. Ya. Sosnovskikhg, D. L. Obydennovg, S. A. Usachevg

a N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences
b Novosibirsk State University
c Saint-Petersburg State Forest Academy
d Saint Petersburg State University
e A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow
f I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, Ekaterinburg
g Ural Federal University named after the First President of Russia B. N. Yeltsin, Ekaterinburg
h Institute of Physiologically Active Compounds RAS, Chernogolovka
i Lomonosov Moscow State University, Faculty of Chemistry
j A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
k N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
l Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow region
m Boreskov Institute of Catalysis SB RAS, Novosibirsk
n Tomsk State University, Department of Chemistry

Abstract: 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 $\mathrm{CF}_3$-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 $\mathrm{N}$-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, $\alpha$-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.

Funding Agency Grant Number
Russian Science Foundation 18-13-00173
Russian Foundation for Basic Research 19-53-53003
16-29-10762 офи_м
Ministry of Education and Science of the Russian Federation 0090-2017-0023

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English version:
Russian Chemical Reviews, 2019, 88:5, 425–569

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Document Type: Article
Received: 16.11.2018

Citation: 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”, Usp. Khim., 88:5 (2019), 425–569; Russian Chem. Reviews, 88:5 (2019), 425–569

Citation in format AMSBIB
\by 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
\paper Organofluorine chemistry: promising growth areas and challenges
\jour Usp. Khim.
\yr 2019
\vol 88
\issue 5
\pages 425--569
\jour Russian Chem. Reviews
\yr 2019
\vol 88
\issue 5
\pages 425--569

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