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Organofluorine chemistry: Promising growth areas and challenges. / Politanskaya, Larisa V.; Selivanova, Galina A.; Panteleeva, Elena V. et al.

In: Russian Chemical Reviews, Vol. 88, No. 5, 01.01.2019, p. 425-569.

Research output: Contribution to journal › Review article › peer-review

Harvard

Politanskaya, LV, Selivanova, GA, Panteleeva, EV, Tretyakov, EV, Platonov, VE, Nikul'Shin, PV, Vinogradov, AS, Zonov, YV, Karpov, VM, Mezhenkova, TV, Vasilyev, AV, Koldobskii, AB, Shilova, OS, Morozova, SM, Burgart, YV, Shchegolkov, EV, Saloutin, VI, Sokolov, VB, Aksinenko, AY, Nenajdenko, VG, Moskalik, MY, Astakhova, VV, Shainyan, BA, Tabolin, AA, Ioffe, SL, Muzalevskiy, VM, Balenkova, ES, Shastin, AV, Tyutyunov, AA, Boiko, VE, Igumnov, SM, Dilman, AD, Adonin, NY, Bardin, VV, Masoud, SM, Vorobyeva, DV, Osipov, SN, Nosova, EV, Lipunova, GN, Charushin, VN, Prima, DO, Makarov, AG, Zibarev, AV, Trofimov, BA, Sobenina, LN, Belyaeva, KV, Sosnovskikh, VY, Obydennov, DL & Usachev, SA 2019, 'Organofluorine chemistry: Promising growth areas and challenges', Russian Chemical Reviews, vol. 88, no. 5, pp. 425-569. https://doi.org/10.1070/RCR4871

APA

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

Vancouver

Politanskaya LV, Selivanova GA, Panteleeva EV, Tretyakov EV, Platonov VE, Nikul'Shin PV et al. Organofluorine chemistry: Promising growth areas and challenges. Russian Chemical Reviews. 2019 Jan 1;88(5):425-569. doi: 10.1070/RCR4871

Author

Politanskaya, Larisa V. ; Selivanova, Galina A. ; Panteleeva, Elena V. et al. / Organofluorine chemistry: Promising growth areas and challenges. In: Russian Chemical Reviews. 2019 ; Vol. 88, No. 5. pp. 425-569.

BibTeX

@article{b37145df65324c1b913fe4e25fc078ae,
title = "Organofluorine chemistry: Promising growth areas and challenges",
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.",
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",
author = "Politanskaya, {Larisa V.} and Selivanova, {Galina A.} and Panteleeva, {Elena V.} and Tretyakov, {Evgeny V.} and Platonov, {Vyacheslav E.} and Nikul'Shin, {Pavel V.} and Vinogradov, {Andrey S.} and Zonov, {Yaroslav V.} and Karpov, {Victor M.} and Mezhenkova, {Tatyana V.} and Vasilyev, {Aleksander V.} and Koldobskii, {Andrei B.} and Shilova, {Olga S.} and Morozova, {Sofia M.} and Burgart, {Yanina V.} and Shchegolkov, {Evgeny V.} and Saloutin, {Victor I.} and Sokolov, {Vladimir B.} and Aksinenko, {Aleksey Yu} and Nenajdenko, {Valentine G.} and Moskalik, {Mikhail Yu} and Astakhova, {Vera V.} and Shainyan, {Bagrat A.} and Tabolin, {Andrey A.} and Ioffe, {Sema L.} and Muzalevskiy, {Vasiliy M.} and Balenkova, {Elizaveta S.} and Shastin, {Alexey V.} and Tyutyunov, {Andrey A.} and Boiko, {Vladimir E.} and Igumnov, {Sergei M.} and Dilman, {Alexander D.} and Adonin, {Nicolay Yu} and Bardin, {Vadim V.} and Masoud, {Salekh M.} and Vorobyeva, {Daria V.} and Osipov, {Sergey N.} and Nosova, {Emiliya V.} and Lipunova, {Galina N.} and Charushin, {Valery N.} and Prima, {Darya O.} and Makarov, {Arkady G.} and Zibarev, {Andrey V.} and Trofimov, {Boris A.} and Sobenina, {Lyubov N.} and Belyaeva, {Kseniya V.} and Sosnovskikh, {Vyacheslav Ya} and Obydennov, {Dmitrii L.} and Usachev, {Sergey A.}",
note = "Chapter 2 (by L.V.Politanskaya, G.A.Selivanova, E.V.Panteleeva and E.V.Tretyakov) was written with the financial support of the Russian Science Foundation (RSF) (Project No. 18-13-00173) and the Russian Foundation for Basic Research (RFBR) (Project No. 19-53-53003); chapter 7 (by Ya.V.Burgart, E.V.Shchegolkov and V.I.Saloutin) was written with the financial support of the RSF (Project No. 16-13-10255); chapter 8 (by V.B.Sokolov and A.Yu.Aksinenko) was prepared within the state assignment of the Ministry of Education and Science of Russia for 2018 +/- 2020 (theme No. 0090-2017-0023); chapter 11 (by A.A.Tabolin and S.L.Ioffe) was written with the financial support of the RFBR (Project No. 18-03-00810); chapter 12 (by V.M.Muzalevskiy, E.S.Balenkova, A.V.Shastin and V.G.Nenajdenko) was written with the financial support of the RFBR (Project No. 16-03-00936-a); chapter 15 (by N.Yu.Adonin and V.V.Bardin) was written with the financial support of the RFBR (Project No. 16-29-10762 ofi_m); chapter 16 (by S.N.Osipov, D.V.Vorobyeva and S.M.Masoud) was written with the financial support of the RSF (Project No. 16-13-10364); chapter 17 (by E.V.Nosova, G.N.Lipunova and V.N.Charushin) was written with the financial support of the RSF (Project No. 15-13-00077-P) and within the state assignment of the Ministry of Education and Science of Russia for 2018 +/- 2020 (theme No. 4.6351.2017/8.9); chapter 19 was written with the financial support of the RFBR (by K.V.Belyaeva, Project No. 1803-00762) and within the state assignment of the Ministry of Education and Science of Russia (B.A.Trofimov and L.N.Sobenina; theme No.V.44.5.6); chapter 20 (by V.Ya.Sosnovskikh, D.L.Obydennov and S.A.Usachev) was written with the financial support of the RFBR (Project No. 17-03-00340).",
year = "2019",
month = jan,
day = "1",
doi = "10.1070/RCR4871",
language = "English",
volume = "88",
pages = "425--569",
journal = "Russian Chemical Reviews",
issn = "0036-021X",
publisher = "Turpion Ltd.",
number = "5",

}

RIS

TY - JOUR

T1 - Organofluorine chemistry: Promising growth areas and challenges

AU - Politanskaya, Larisa V.

AU - Selivanova, Galina A.

AU - Panteleeva, Elena V.

AU - Tretyakov, Evgeny V.

AU - Platonov, Vyacheslav E.

AU - Nikul'Shin, Pavel V.

AU - Vinogradov, Andrey S.

AU - Zonov, Yaroslav V.

AU - Karpov, Victor M.

AU - Mezhenkova, Tatyana V.

AU - Vasilyev, Aleksander V.

AU - Koldobskii, Andrei B.

AU - Shilova, Olga S.

AU - Morozova, Sofia M.

AU - Burgart, Yanina V.

AU - Shchegolkov, Evgeny V.

AU - Saloutin, Victor I.

AU - Sokolov, Vladimir B.

AU - Aksinenko, Aleksey Yu

AU - Nenajdenko, Valentine G.

AU - Moskalik, Mikhail Yu

AU - Astakhova, Vera V.

AU - Shainyan, Bagrat A.

AU - Tabolin, Andrey A.

AU - Ioffe, Sema L.

AU - Muzalevskiy, Vasiliy M.

AU - Balenkova, Elizaveta S.

AU - Shastin, Alexey V.

AU - Tyutyunov, Andrey A.

AU - Boiko, Vladimir E.

AU - Igumnov, Sergei M.

AU - Dilman, Alexander D.

AU - Adonin, Nicolay Yu

AU - Bardin, Vadim V.

AU - Masoud, Salekh M.

AU - Vorobyeva, Daria V.

AU - Osipov, Sergey N.

AU - Nosova, Emiliya V.

AU - Lipunova, Galina N.

AU - Charushin, Valery N.

AU - Prima, Darya O.

AU - Makarov, Arkady G.

AU - Zibarev, Andrey V.

AU - Trofimov, Boris A.

AU - Sobenina, Lyubov N.

AU - Belyaeva, Kseniya V.

AU - Sosnovskikh, Vyacheslav Ya

AU - Obydennov, Dmitrii L.

AU - Usachev, Sergey A.

N1 - Chapter 2 (by L.V.Politanskaya, G.A.Selivanova, E.V.Panteleeva and E.V.Tretyakov) was written with the financial support of the Russian Science Foundation (RSF) (Project No. 18-13-00173) and the Russian Foundation for Basic Research (RFBR) (Project No. 19-53-53003); chapter 7 (by Ya.V.Burgart, E.V.Shchegolkov and V.I.Saloutin) was written with the financial support of the RSF (Project No. 16-13-10255); chapter 8 (by V.B.Sokolov and A.Yu.Aksinenko) was prepared within the state assignment of the Ministry of Education and Science of Russia for 2018 +/- 2020 (theme No. 0090-2017-0023); chapter 11 (by A.A.Tabolin and S.L.Ioffe) was written with the financial support of the RFBR (Project No. 18-03-00810); chapter 12 (by V.M.Muzalevskiy, E.S.Balenkova, A.V.Shastin and V.G.Nenajdenko) was written with the financial support of the RFBR (Project No. 16-03-00936-a); chapter 15 (by N.Yu.Adonin and V.V.Bardin) was written with the financial support of the RFBR (Project No. 16-29-10762 ofi_m); chapter 16 (by S.N.Osipov, D.V.Vorobyeva and S.M.Masoud) was written with the financial support of the RSF (Project No. 16-13-10364); chapter 17 (by E.V.Nosova, G.N.Lipunova and V.N.Charushin) was written with the financial support of the RSF (Project No. 15-13-00077-P) and within the state assignment of the Ministry of Education and Science of Russia for 2018 +/- 2020 (theme No. 4.6351.2017/8.9); chapter 19 was written with the financial support of the RFBR (by K.V.Belyaeva, Project No. 1803-00762) and within the state assignment of the Ministry of Education and Science of Russia (B.A.Trofimov and L.N.Sobenina; theme No.V.44.5.6); chapter 20 (by V.Ya.Sosnovskikh, D.L.Obydennov and S.A.Usachev) was written with the financial support of the RFBR (Project No. 17-03-00340).

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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.

AB - 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.

KW - FLUORINE-CONTAINING HETEROCYCLES

KW - BIOLOGICALLY-ACTIVE AMIDES

KW - ONE-POT SYNTHESIS

KW - BETA-ARYL ENAMINES

KW - CONTAINING 2-ARYLHYDRAZONO-1,3-DICARBONYL COMPOUNDS

KW - PALLADIUM-CATALYZED DIFLUOROMETHYLATION

KW - DIRECT NUCLEOPHILIC DIFLUOROMETHYLATION

KW - COPPER-MEDIATED DIFLUOROMETHYLATION

KW - GRUBBS 2ND-GENERATION CATALYST

KW - ASYMMETRIC MICHAEL ADDITION

UR - http://www.scopus.com/inward/record.url?scp=85066251313&partnerID=8YFLogxK

UR - https://www.elibrary.ru/item.asp?id=41801075

UR - https://www.mendeley.com/catalogue/6d187c55-cd3c-312a-9ce2-5d7406c6c721/

U2 - 10.1070/RCR4871

DO - 10.1070/RCR4871

M3 - Review article

AN - SCOPUS:85066251313

VL - 88

SP - 425

EP - 569

JO - Russian Chemical Reviews

JF - Russian Chemical Reviews

SN - 0036-021X

IS - 5

ER -

ID: 20344417