Russian Journal of Organic Chemistry

, Volume 53, Issue 5, pp 800–804 | Cite as

Potassium fluoride for one-pot desilylation and the Sonogashira coupling of ethynylsilanes and buta-1,3-diynylsilanes

  • A. G. Lyapunova
  • A. S. D’yachenko
  • N. A. Danilkina
Short Communications


Opportunities were outlined for application of available KF as a source of fluoride ions and a base in desilylation/the Sonogashira coupling reactions under conditions of a one-pot process.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Sonogashira, K., Tohda, Y., and Hagihara, N., Tetrahedron Lett., 1975, vol. 16, p. 4467.CrossRefGoogle Scholar
  2. 2.
    Thomas, A.M., Sujatha, A., and Anilkumar, G., RSC Adv., 2014, vol. 4, p. 21688.CrossRefGoogle Scholar
  3. 3.
    Schaub, T.A., Kivala, M., Metal-Catalyzed Cross-Coupling Reactions and More, De Meijere, A., Bräse, S., and Oestreich, M., Eds., Weinheim: Wiley-VCH, 2014, p. 731.Google Scholar
  4. 4.
    Hatanaka, Y. and Hiyama, T., J. Org. Chem., 1988, vol. 53, p. 918.CrossRefGoogle Scholar
  5. 5.
    Nishihara, Y., Ikegashira, K., Mori, A., and Hiyama, T., Chem. Lett., 1997, vol. 12, p. 1233.CrossRefGoogle Scholar
  6. 6.
    Halbes, U., Bertus, P., and Pale, P., Tetrahedron Lett., 2001, vol. 42, p. 8641.CrossRefGoogle Scholar
  7. 7.
    Danilkina, N.A., Bräse, S., and Balova, I.A., Synlett., 2011, p. 517.Google Scholar
  8. 8.
    Danilkina, N.A., Kulyashova, A.E., Khlebnikov, A.F., Bräse, S., and Balova, I.A., J. Org. Chem., 2014, vol. 79, p. 9018.CrossRefGoogle Scholar
  9. 9.
    Danilkina, N., Nieger, M., Selivanov, S., Bräse, S., and Balova, I., Eur. J. Org. Chem., 2012, p. 5660.Google Scholar
  10. 10.
    Danilkina, N.A., Lyapunova, A.G., Khlebnikov, A.F., Starova, G.L., Bräse, S., and Balova, I.A., J. Org. Chem., 2015, vol. 80, p. 5546.CrossRefGoogle Scholar
  11. 11.
    Danilkina, N.A., Gurskaya, L.Y., Vasilyev, A.V., and Balova, I.A., Eur. J. Org. Chem., 2016, p. 739.Google Scholar
  12. 12.
    Kinashi, N., Sakaguchi, K., Katsumura, S., and Shinada, T., Tetrahedron Lett., 2016, vol. 57, p. 129.CrossRefGoogle Scholar
  13. 13.
    Ishikawa, T., Seto, M., Banno, H., Kawakita, Y., Oorui, M., Taniguchi, T., Ohta, Y., Tamura, T., Nakayama, A., Miki, H., Kamiguchi, H., Tanaka, T., Habuka, N., Sogabe, S., Yano, J., Aertgeerts, K., and Kamiyama, K., J. Med. Chem., 2011, vol. 54, p. 8030.CrossRefGoogle Scholar
  14. 14.
    Hosseinzadeh, R., Mohadjerani, M., Tavakoli, R., and Alikarami, M., Synth. Commun., 2010, vol. 40, p. 282.CrossRefGoogle Scholar
  15. 15.
    Vinogradova, O.V., Sorokoumov, V.N., Vasilevskii, S.F., and Balova, I.A., Russ. Chem. Bull., 2008, vol. 57, p. 1725. doi 10.1007/s11172-008-0228-zCrossRefGoogle Scholar
  16. 16.
    Danilkina, N.A., Vlasov, P.S., Vodianik, S.M., Kruchinin, A.A., Vlasov, Y.G., and Balova, I.A., Beilst. J. Org. Chem., 2015, vol. 11, p. 373.CrossRefGoogle Scholar
  17. 17.
    Lyapunova, A.G., Danilkina, N.A., Khlebnikov, A.F., Köberle, B., Bräse, S., and Balova, I.A., Eur. J. Org. Chem., 2016, p. 4842.Google Scholar
  18. 18.
    Imperio, D., Pirali, T., Galli, U., Pagliai, F., Cafici, L., Canonico, P.L., Sorba, G., Genazzani, A.A., and Tron, G.C., Bioorg. Med. Chem., 2007, vol. 15, p. 6748. doi 10.1016/j.bmc.2007.08.020CrossRefGoogle Scholar
  19. 19.
    Hess, W. and Burton, J.W., Chem. Eur. J., 2010, vol. 16, p. 12303.CrossRefGoogle Scholar
  20. 20.
    Zheng, R., Wang, Y., and Zhang, L., Tetrahedron Lett., 2015, vol. 56, p. 3144.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • A. G. Lyapunova
    • 1
  • A. S. D’yachenko
    • 1
  • N. A. Danilkina
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

Personalised recommendations