Advertisement

Russian Journal of General Chemistry

, Volume 88, Issue 10, pp 2197–2199 | Cite as

Pd–Cu-Catalyzed Synthesis of Alk-5-en-7-yn-2-ones

  • R. N. ShakhmaevEmail author
  • A. Sh. Sunagatullina
  • E. A. Abdullina
  • V. V. Zorin
Letters to the Editor

Abstract

Stereoselective synthesis of (E)- and (Z)-alk-5-en-7-in-2-ones was performed by cross-coupling of alkynes with 6-chlorohex-5-en-2-one stereoisomers in the presence of PdCl2(PrCN)2 complex and CuI in piperidine.

Keywords

cross-coupling reaction Sonogashira reaction vinyl chloride alk-5-en-7-yn-2-ones 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Dembitsky, V.M., Levitsky, D.O., Gloriozova, T.A., and Poroikov, V.V., Nat. Prod. Commun., 2006, vol. 1, p.773.Google Scholar
  2. 2.
    Dembitsky, V.M., Lipids, 2006, vol. 41, p. 883. doi 10.1007/s11745-006-5044-3CrossRefGoogle Scholar
  3. 3.
    Siddiq, A. and Dembitsky, V., Anti-Cancer Agents Med. Chem., 2008, vol. 8, p. 132. doi 10.2174/187152008783497073CrossRefGoogle Scholar
  4. 4.
    Mejia, E.J., Magranet, L.B., De Voogd, N.J., TenDyke, K., Qiu, D., Shen, Y.Y., Zhou, Z., and Crews, P., J. Nat. Prod., 2013, vol. 76, p. 425. doi 10.1021/np3008446CrossRefGoogle Scholar
  5. 5.
    Zhou, Z.-F., Menna, M., Cai, Y.-S., and Guo, Y.-W., Chem. Rev., 2015, vol. 115, p. 1543. doi 10.1021/cr4006507CrossRefGoogle Scholar
  6. 6.
    Shakhmaev, R.N., Sunagatullina, A.Sh., Alieva, R.M., and Zorin, V.V., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, p. 2472. doi 10.1134/S1070363217100310CrossRefGoogle Scholar
  7. 7.
    Metal-Catalyzed Cross-Coupling Reactions and More, de Meijere, A., Bräse, S., and Oestreich, M., Eds., New-York: Wiley-VCH, 2014. 1576 p.Google Scholar
  8. 8.
    Shakhmaev, R.N., Ishbaeva, A.U., and Zorin, V.V., Russ. J. Org. Chem., 2012, vol. 48, no. 7, p. 908. doi 10.1134/S1070428012070032CrossRefGoogle Scholar
  9. 9.
    Takhautdinova, A.U., Mindiyarova, E.R., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Appl. Chem., 2011, vol. 84, no. 3, p. 504. doi 10.1134/S1070427211030293CrossRefGoogle Scholar
  10. 10.
    Shakhmaev, R.N., Sunagatullina, A.Sh., Akimova, D.A., and Zorin, V.V., Russ. J. Org. Chem., 2017, vol. 53, no. 4, p. 615. doi 10.1134/S1070428017040194CrossRefGoogle Scholar
  11. 11.
    Homogeneous catalysis for unreactive bond activation, Shi, Z.-J., Ed., Hoboken: John Wiley & Sons, 2014.Google Scholar
  12. 12.
    Shakhmaev, R.N., Sunagatullina, A.Sh., and Zorin, V.V., Russ. J. Gen. Chem., 2016, vol. 86, no. 8, p. 1969. doi 10.1134/S107036321608034XCrossRefGoogle Scholar
  13. 13.
    Shakhmaev, R.N., Sunagatullina, A.Sh., and Zorin, V.V., Chem. Nat. Compd., 2017, vol. 53, no. 1, p. 128. doi 10.1007/s10600-017-1925-3CrossRefGoogle Scholar
  14. 14.
    Alami, M., Crousse, B., and Ferri, F., J. Organomet. Chem., 2001, vol. 624, p. 114. doi 10.1016/S0022-328X (00)00909-8CrossRefGoogle Scholar
  15. 15.
    Sunagatullina, A.S., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Gen. Chem., 2013, vol. 83, no. 1, p. 148. doi 10.1134/S1070363213010313CrossRefGoogle Scholar
  16. 16.
    Shakhmaev, R.N., Sunagatullina, A.Sh., Emyshaeva, N.V., and Zorin, V.V., Chem. Nat. Compd., 2015, vol. 51, no. 1, p. 127. doi 10.1007/s10600-015-1217-8CrossRefGoogle Scholar
  17. 17.
    Sunagatullina, A.S., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Org. Chem., 2013, vol. 49, no. 5, p. 730. doi 10.1134/S1070428013050163CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • R. N. Shakhmaev
    • 1
    Email author
  • A. Sh. Sunagatullina
    • 1
  • E. A. Abdullina
    • 1
  • V. V. Zorin
    • 1
  1. 1.Ufa State Petroleum Technological UniversityUfaRussia

Personalised recommendations