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. Nenajdenko; Mikhail 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

doi:10.1070/RCR4871

Organofluorine chemistry: Promising growth areas and challenges

Переведенное название: Перспективные точки роста и вызовы фторорганической химии

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

Результат исследования: Научные публикации в периодических изданиях › обзорная статья › рецензирование

73 Цитирования (Scopus)

Аннотация

В настоящее время химия фторорганических соединений является одной из лидирующих и быстро прогрессирующих областей органической химии. Наличие в молекуле этого элемента в значительной степени определяет ее специфические химические и биологические свойства. Данный тематический выпуск объединяет различные направления фторорганической химии, которые наиболее активно развиваются за последние 15-20 лет. В нем представлены реакции нуклеофильного замещения и гетероциклизации c участием фторированных аренов и хинонов, а также скелетные катионоидные перегруппировки в ряду полифтораренов. Рассмотрены превращения с участием CF3-замещенных карбокатионов и катион-радикалов. Обсуждены процессы гетероциклизации и окислительного присоединения производных трифторацетамида, трансформации органического фрагмента полифторированных органоборанов и боратов с сохранением связи углерод-бор. Особое внимание уделено каталитическому олефинированию с использованием фреонов как эффективному методу синтеза фторсодержащих соединений. Показано применение несимметричных фторсодержащих N-гетероциклических карбеновых лигандов в катализе метатезиса олефинов. Рассмотрены различные классы фторорганических соединений, такие как полифторированные арены и 1,2-диаминобензолы, 1-галоген-2-трифторацетилацетилены, α-фторнитросоединения, фторсодержащие гетероциклы, 2-гидразинилиден-1,3-дикарбонильные производные, имины и силаны. Показаны потенциальные области практического применения фторорганических соединений, включая фундаментальную органическую химию, науку о материалах и биомедицину. Библиография - 1019 ссылок.

Переведенное название	Перспективные точки роста и вызовы фторорганической химии
Язык оригинала	английский
Страницы (с-по)	425-569
Число страниц	145
Журнал	Russian Chemical Reviews
Том	88
Номер выпуска	5
DOI	https://doi.org/10.1070/RCR4871
Состояние	Опубликовано - 1 янв. 2019

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1.04 ХИМИЧЕСКИЕ НАУКИ

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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

@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",

}

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, том. 88, № 5, стр. 425-569. https://doi.org/10.1070/RCR4871

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

В: Russian Chemical Reviews, Том 88, № 5, 01.01.2019, стр. 425-569.

Результат исследования: Научные публикации в периодических изданиях › обзорная статья › рецензирование

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

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 -