Loading [MathJax]/jax/output/SVG/config.js
Mendeleev Communications
RUS  ENG    JOURNALS   PEOPLE   ORGANISATIONS   CONFERENCES   SEMINARS   VIDEO LIBRARY   PACKAGE AMSBIB  
General information
Latest issue
Archive

Search papers
Search references

RSS
Latest issue
Current issues
Archive issues
What is RSS



Mendeleev Commun.:
Year:
Volume:
Issue:
Page:
Find






Personal entry:
Login:
Password:
Save password
Enter
Forgotten password?
Register


Mendeleev Communications, 2015, Volume 25, Issue 4, Pages 239–244
DOI: https://doi.org/10.1016/j.mencom.2015.07.001
(Mi mendc2365)
 

This article is cited in 35 scientific papers (total in 35 papers)

Focus Article

Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents

A. D. Dilman, V. V. Levin

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: α-Fluorinated organosilanes Me3SiCF2X serve as versatile reagents for the synthesis of organofluorine compounds. Most reactions start from Lewis base activation of carbon–silicon bond through the intermediacy of five-coordinate siliconate species. Interaction of these silanes with suitable electrophiles leads to products of nucleophilic fluoroalkylation; an alternative pathway involves generation of difluorocarbene. These reagents can also be considered as equivalents of difluoromethylene radical anion and bis(carbanion) when carbon–heteroatom bond C–X is activated.
Document Type: Article
Language: English


Citation: A. D. Dilman, V. V. Levin, “Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents”, Mendeleev Commun., 25:4 (2015), 239–244
Linking options:
  • https://www.mathnet.ru/eng/mendc2365
  • https://www.mathnet.ru/eng/mendc/v25/i4/p239
  • This publication is cited in the following 35 articles:
    1. Sabrina Hoford, Julius Jan, Jeffrey N. Johnston, Travis Dudding, “Elucidating Fluorine Steering Effects in Diels‐Alder Reactions Interfaced with Charge‐Enhanced Reactivity”, Eur J Org Chem, 2025  crossref
    2. Zhi Tu, Jinsheng Yu, Jian Zhou, “Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis”, Chinese Journal of Organic Chemistry, 43:10 (2023), 3491  crossref
    3. Egor A. Ilin, Vladimir O. Smirnov, Alexander D. Dilman, “Generation of fluoro(thio)carbenes from Me3SiCF2SAr”, Journal of Fluorine Chemistry, 261-262 (2022), 110025  crossref
    4. Koki Maruno, Kiyoteru Niina, Osamu Nagata, Norio Shibata, “Synthesis of an Eccentric Electron-Deficient Fluorinated Motif, Tetrafluoro-λ6-sulfanyl gem-Difluorocyclopropenes”, Org. Lett., 24:8 (2022), 1722  crossref
    5. Anna Pees, Maria J.W.D Vosjan, Neil Vasdev, Albert D. Windhorst, Danielle J. Vugts, “Fluorine-18 labelled Ruppert–Prakash reagent ([18F]Me3SiCF3) for the synthesis of 18F-trifluoromethylated compounds”, Chem. Commun., 57:43 (2021), 5286  crossref
    6. Vyacheslav I. Supranovich, Alexander D. Volodin, Alexander A. Korlyukov, Jinbo Hu, Alexander D. Dilman, “Reaction of (bromodifluoromethyl)trimethylsilane with HMPA: Structural studies”, Journal of Fluorine Chemistry, 250 (2021), 109881  crossref
    7. A. M. Semenova, M. A. Ezhikova, M. I. Kodess, A. Ya. Zapevalov, A. V. Pestov, “Phosgene-free synthesis of symmetric bis(polyfluoroalkyl) carbonates”, Mendeleev Commun., 31:2 (2021), 257–258  mathnet  crossref
    8. Dmitriy M. Volochnyuk, Oleksandr O. Grygorenko, Emerging Fluorinated Motifs, 2020, 135  crossref
    9. Egor A. Ilin, Vladimir O. Smirnov, Alexander D. Volodin, Alexander A. Korlyukov, Alexander D. Dilman, “ortho-Dialkylamino arylboranes as efficient reagents for difluorocarbene trapping”, Chem. Commun., 56:52 (2020), 7140  crossref
    10. Andrés García-Domínguez, Thomas H. West, Johann J. Primozic, Katie M. Grant, Craig P. Johnston, Grant G. Cumming, Andrew G. Leach, Guy C. Lloyd-Jones, “Difluorocarbene Generation from TMSCF3: Kinetics and Mechanism of NaI-Mediated and Si-Induced Anionic Chain Reactions”, J. Am. Chem. Soc., 142:34 (2020), 14649  crossref
    11. Vyacheslav I Supranovich, Vitalij V Levin, Alexander D Dilman, “Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers”, Beilstein J. Org. Chem., 16 (2020), 1550  crossref
    12. 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”, Russian Chem. Reviews, 88:5 (2019), 425–569  mathnet  mathnet  crossref  isi  scopus
    13. Liubov I. Panferova, Marina I. Struchkova, Alexander D. Dilman, “Light‐Promoted Allylation of Iododifluoromethylated Alcohols”, Eur J Org Chem, 2018:27-28 (2018), 3834  crossref
    14. Vyacheslav I. Supranovich, Vitalij V. Levin, Marina I. Struchkova, Alexander D. Dilman, “Photocatalytic Reductive Fluoroalkylation of Nitrones”, Org. Lett., 20:3 (2018), 840  crossref
    15. Vyacheslav I Supranovich, Vitalij V Levin, Marina I Struchkova, Jinbo Hu, Alexander D Dilman, “Visible light-mediated difluoroalkylation of electron-deficient alkenes”, Beilstein J. Org. Chem., 14 (2018), 1637  crossref
    16. Artem V. Tsymbal, Vitalij V. Levin, Marina I. Struchkova, Vladimir A. Kokorekin, Alexander A. Korlyukov, Alexander D. Dilman, “Reductive silylation of gem-difluorinated phosphonium salts”, Journal of Fluorine Chemistry, 205 (2018), 58  crossref
    17. Alexander D. Dilman, Vitalij V. Levin, “Difluorocarbene as a Building Block for Consecutive Bond-Forming Reactions”, Acc. Chem. Res., 51:5 (2018), 1272  crossref
    18. Liubov I. Panferova, Grigory N. Chernov, Vitalij V. Levin, Vladimir A. Kokorekin, Alexander D. Dilman, “Photoredox mediated annelation of iododifluoromethylated alcohols with 1,1-diarylethylenes”, Tetrahedron, 74:50 (2018), 7136  crossref
    19. R. O. Iakovenko, A. D. Dilman, “Synthesis of halodifluoromethyl-substituted phosphines”, Mendeleev Commun., 28:4 (2018), 396–397  mathnet  crossref
    20. Liubov I. Panferova, Vladimir O. Smirnov, Vitalij V. Levin, Vladimir A. Kokorekin, Marina I. Struchkova, Alexander D. Dilman, “Synthesis of 3-Fluoroindoles via Photoredox Catalysis”, J. Org. Chem., 82:1 (2017), 745  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
    Mendeleev Communications
    Statistics & downloads:
    Abstract page:28
    Full-text PDF :7
     
      Contact us:
     Terms of Use  Registration to the website  Logotypes © Steklov Mathematical Institute RAS, 2025