Skip to main content
SpringerLink
Log in

Synthesis of functionalized difluoronaphthalenes by regioselective C—H functionalization of 2,3-difluoronaphthalene

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

2,3-Difluoronaphthalene (1) was selectively converted into 1-methyl-, 1,4-dimethyl-, 1-acetyl-, 1-acetyl-4-methyl-, 1-formyl-, and 1-carboxyl-substituted 2,3-difluoronaphthalenes using lithiation with BuLi as a key step. Nitration and bromination of compound 1 predominantly gave 6,7-difluoro-1-nitronaphthalene and 1-bromo-6,7-difluoronaphthalene, respectively. Regioselectivity of acylation of compound 1 and 2,3-difluoro-1,4-dimethylnaphthalene with AcCl in the presence of AlCl3 dramatically depended on the order of mixing and addition of the reagents. Under the optimized conditions, the yields of 1-(6,7-difluoronaphthalen-1-yl) ethanones and 1-(6,7-difluoronaphthalen-2-yl)ethanones reached 68–93%.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Organofluorine Compounds in Medical Chemistry and Biomedical Application, Eds R. Filler, Y. Kobayashi, L. M. Yagupolskii, Elsevier, Amsterdam, 1993, 386 pp.

    Google Scholar 

  2. T. Abe, S. Nagase, in Preparation, Properties and Industrial Application of Organofluorine Compounds, Ed. R. E. Banks, J. Willey and Sons, New York, 1982, p. 19.

  3. P. Kirsch, Modern Fluoroorganic Chemistry. Synthesis, Reactivity, Application, Wiley-VCH, Weiheim, 2004, 308 pp.

    Book  Google Scholar 

  4. E. P. Gillis, K. J. Eastman, M. D. Donnelly, N. A. Meanwell, J. Med. Chem., 2015, 58, 8315.

    Article  CAS  Google Scholar 

  5. Y. Znou, J. Wang, Z. Gu, S. Wang, W. Zhu, J. L. Acena, V. A. Soloshonok, K. Izawa, H. Liu, Chem. Rev., 2016, 116, 422.

    Article  Google Scholar 

  6. R. T. Khusnutdinov, T. M. Egorova, R. I. Aminov, U. M. Dzhemilev, Mendeleev Commun., 2018, 28, 644.

    Article  CAS  Google Scholar 

  7. 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. Iofe, 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, Russ. Chem. Rev., 2019, 88, 425–569.

    Article  CAS  Google Scholar 

  8. E. T. Akin, M. Erdagan, A. Dastan, N. Sarocogly, Tetrahedron Lett., 2017, 73, 5537.

    Article  CAS  Google Scholar 

  9. C. Song, C. Yang, H. Zeng, W. Zhang, S. Guo, J. Znu, Org. Lett., 2018, 20, 3819.

    Article  CAS  Google Scholar 

  10. M. James, J. L. Schwarz, F. Strieth-Kathof, B. Wibbeling, F. Glorius, J. Am. Chem. Soc., 2018, 140, 8624.

    Article  CAS  Google Scholar 

  11. H.-T. Xie, D.-C. Zhou, Y.-W. Mai, L. Huo, P.-F. Yao, S.-L. Huang, H.-G. Wang, Z.-S. Huang, L.-Q. Gu, RSC Adv., 2017, 7, 20919.

    Article  CAS  Google Scholar 

  12. Y. Tokao, T. Masuoka, Tetrahedron Lett., 2014, 55, 4564.

    Article  Google Scholar 

  13. N. Koppanathi, K. Swamy, G. Kumata, Org. Biomol. Chem., 2016, 14, 5079.

    Article  CAS  Google Scholar 

  14. G.-Y. Lo, M. P. Kumar, H.-K. Chang, S.-F. Lush, R.-S. Liu, J. Org. Chem., 2005, 70, 10482.

    Article  CAS  Google Scholar 

  15. T. M. Krulle, O. Barba, S. H. Davis, G. Dawson, M. J. Procter, T. Staroske, G. H. Thomas, Tetrahedron Lett., 2007, 48, 1537.

    Article  Google Scholar 

  16. J. R. Tagat, S. W. McCombie, D. V. Nazareno, C. D. Boyle, J. A. Kozlowski, S. Chackalamannil, H. Josiene, Y. Wang, G. Zhou, J. Org. Chem., 2002, 67, 1171–1177.

    Article  CAS  Google Scholar 

  17. M. Ballantine, M. L. Menard, W. Tam, J. Org. Chem., 2009, 74, 7570.

    Article  CAS  Google Scholar 

  18. K. R. Deaton, M. S. Gin, Org. Lett., 2003, 5, 2477–2480.

    Article  CAS  Google Scholar 

  19. D. H. Kim, S. U. Son, Y. K. Chung, Org. Lett., 2003, 5, 3151–3153.

    Article  CAS  Google Scholar 

  20. F. Jafarpour, H. Hazrati, S. Nouraldinmousa, Org. Lett., 2013, 15, 3816.

    Article  CAS  Google Scholar 

  21. C. M. Kane, T. B. Meyers, X. Yu, M. Gerken, M. Etzkorn, Eur. J. Org. Chem., 2011, 2669.

    Google Scholar 

  22. V. N. Charushin, S. K. Kotovskay, S. A. Romanova, O. N. Chupakhin, Yu. V. Tomilov, O. M. Nefedov, Mendeleev Commun., 2005, 15, 45.

    Article  Google Scholar 

  23. P. Nussbaumen, G. Dorfstatter, I. Leither, K. Mraz, H. Vyplel, A. Stutz, J. Med. Chem., 1993, 36, 280.

    Article  Google Scholar 

  24. J.-P. Gourvies, R. Ruzziconi, L. Vilarroing, J. Org. Chem., 2001, 66, 617.

    Article  Google Scholar 

  25. G. Ricci, R. Ruzziconi, J. Org. Chem., 2005, 70, 611.

    Article  CAS  Google Scholar 

  26. Y. Wang, J. Xu, D. J. Burton, J. Org. Chem., 2006, 71, 7780.

    Article  CAS  Google Scholar 

  27. J. T. Repine, D. S. Johnson, A. D. White, D. A. Favor, M. A. Stier, J. Yip, T. Rankin, Q. Ding, S. N. Maiti, Tetrahedron Lett., 2007, 48, 5539.

    Article  CAS  Google Scholar 

  28. A. Furukawa, T. Arita, T. Fukuzaki, M. Mori, T. Honda, S. Satoh, Y. Matsui, K. Wakabayashi, S. Hayaashi, K. Nakamura, K. Araki, M. Kuroha, J. Tanaka, S. Wakimoto, O. Suzuki, J. Ohsumi, Eur. J. Med. Chem., 2012, 54, 522.

    Article  CAS  Google Scholar 

  29. H. Suschitzky, in Advances in Fluorine Chemistry, Eds M. Stacey, J. C. Tatlow, A. G. Sharpe, Butterworths, London, 1965, Vol. 4, p. 1.

    CAS  Google Scholar 

  30. W. Adcock, M. J. S. Dewar, J. Am. Chem. Soc., 1967, 89, 386.

    Article  Google Scholar 

  31. W. Girke, E. D. Bergmann, Chem. Ber., 1976, 109, 1038.

    Article  CAS  Google Scholar 

  32. O. M. Nefedov, A. A. Ivashenko, USSR Author´s Certificate 290900, Bull. Izobtret. [Invention Bull.], 1971, 48, No. 3, 44.

    Google Scholar 

  33. O. M. Nefedov, N. V. Volchkov, Mendeleev Commun., 2006, 16, 121.

    Article  Google Scholar 

  34. N. V. Volchkov, M. B. Lipkind, O. M. Nefedov, Russ. Chem. Bull., 2019, 68, 1232.

    Article  CAS  Google Scholar 

  35. F. J. Weigert, J. Fluorine Chem., 1993, 63, 53.

    Article  CAS  Google Scholar 

  36. D. Doddrell, M. Barfield, W. Adcock, M. Aurangzeb, D. Jordan, J. Chem. Soc., Perkin Trans. 2, 1976, 402.

    Google Scholar 

  37. L. Friedman, R. J. Honour, J. Am. Chem. Soc., 1969, 91, 6344.

    Article  CAS  Google Scholar 

  38. D. D. Dowdy, P. H. Gore, D. N. Waters, J. Chem. Soc., Perkin Trans. 2, 1991, 1149.

    Google Scholar 

  39. G. A. Olah, Friedel-Crafts Chemistry, Wiley-Intersci., New York, 1973.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    N. V. Volchkov, M. B. Lipkind & O. M. Nefedov

Authors
  1. N. V. Volchkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. B. Lipkind
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. M. Nefedov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. V. Volchkov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0270–0279, February, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Volchkov, N.V., Lipkind, M.B. & Nefedov, O.M. Synthesis of functionalized difluoronaphthalenes by regioselective C—H functionalization of 2,3-difluoronaphthalene. Russ Chem Bull 69, 270–279 (2020). https://doi.org/10.1007/s11172-020-2756-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2756-0

Key words

Search

Navigation