Organofluorine chemistry: Promising growth areas and challenges

Larisa V. Politanskaya, Galina A. Selivanova, Elena V. Panteleeva, Evgeny V. Tretyakov, Vyacheslav E. Platonov, Pavel V. Nikul'Shin, Andrey S. Vinogradov, Yaroslav V. Zonov, Victor M. Karpov, Tatyana V. Mezhenkova, Aleksander V. Vasilyev, Andrei B. Koldobskii, Olga S. Shilova, Sofia M. Morozova, Yanina V. Burgart, Evgeny V. Shchegolkov, Victor I. Saloutin, Vladimir B. Sokolov, Aleksey Yu Aksinenko, Valentine G. NenajdenkoMikhail Yu Moskalik, Vera V. Astakhova, Bagrat A. Shainyan, Andrey A. Tabolin, Sema L. Ioffe, Vasiliy M. Muzalevskiy, Elizaveta S. Balenkova, Alexey V. Shastin, Andrey A. Tyutyunov, Vladimir E. Boiko, Sergei M. Igumnov, Alexander D. Dilman, Nicolay Yu Adonin, Vadim V. Bardin, Salekh M. Masoud, Daria V. Vorobyeva, Sergey N. Osipov, Emiliya V. Nosova, Galina N. Lipunova, Valery N. Charushin, Darya O. Prima, Arkady G. Makarov, Andrey V. Zibarev, Boris A. Trofimov, Lyubov N. Sobenina, Kseniya V. Belyaeva, Vyacheslav Ya Sosnovskikh, Dmitrii L. Obydennov, Sergey A. Usachev

Research output: Contribution to journalReview article

37 Citations (Scopus)

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 CF3-substituted carbocations and radical cations are considered. Heterocyclization and oxidative addition reactions of trifluoroacetamide derivatives and trans- formations 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.

Original languageEnglish
Pages (from-to)425-569
Number of pages145
JournalRussian Chemical Reviews
Volume88
Issue number5
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • FLUORINE-CONTAINING HETEROCYCLES
  • BIOLOGICALLY-ACTIVE AMIDES
  • ONE-POT SYNTHESIS
  • BETA-ARYL ENAMINES
  • CONTAINING 2-ARYLHYDRAZONO-1,3-DICARBONYL COMPOUNDS
  • PALLADIUM-CATALYZED DIFLUOROMETHYLATION
  • DIRECT NUCLEOPHILIC DIFLUOROMETHYLATION
  • COPPER-MEDIATED DIFLUOROMETHYLATION
  • GRUBBS 2ND-GENERATION CATALYST
  • ASYMMETRIC MICHAEL ADDITION

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  • Cite this

    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., ... Usachev, S. A. (2019). Organofluorine chemistry: Promising growth areas and challenges. Russian Chemical Reviews, 88(5), 425-569. https://doi.org/10.1070/RCR4871