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Russian Chemical Bulletin

, Volume 53, Issue 3, pp 561–565 | Cite as

Solvent-free palladium-catalyzed addition of diaryl dichalcogenides to alkynes

  • V. P. Ananikov
  • I. P. Beletskaya
Article

Abstract

Solvent-free palladium-catalyzed addition of diaryl disulfides and diselenides to terminal alkynes makes it possible to achieve high stereoselectivity and almost 100% yields in ≈10 min using only 0.1 mol.% catalyst. Both Pd(PPh3)4 and easily available Pd(OAc)2 and PdCl2 can be used in the reaction with an excess of triphenylphosphine. The catalyst and triphenylphosphine are readily recycled for repeated use. The study of the mechanism of the solvent-free catalytic reaction indicates that the process involves binuclear palladium complexes.

vinyl sulfides vinyl selenides stereoselective addition solvent-free reaction homogeneous catalysis palladium complexes 

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References

  1. 1.
    K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025.Google Scholar
  2. 2.
    J. O. Metzger, Angew. Chem., Int. Ed., 1998, 37, 2975.Google Scholar
  3. 3.
    R. J. Morphy, Z. Rankovic, and M. York, Tetrahedron Lett., 2002, 43, 5973.Google Scholar
  4. 4.
    A. Diaz-Ortiz, A. de la Hoz, and F. Langa, Green Chem., 2000, 2, 165.Google Scholar
  5. 5.
    C. R. LeBlond, A. T. Andrews, J. R. Sowa, and Y. Sun, Org. Lett., 2001, 3, 1555.Google Scholar
  6. 6.
    L. M. Klingensmith and N. E. Leadbeater, Tetrahedron Lett., 2003, 44, 765.Google Scholar
  7. 7.
    G. W. Kabalka, L. Wang, R. M. Pagni, M. C. Hair, and V. Namboodiri, Synthesis, 2003, 217.Google Scholar
  8. 8.
    B. Basu, S. Jha, N.K. Mridha, and M. H. Bhuiyan, Tetra hedron Lett., 2002, 43, 7967.Google Scholar
  9. 9.
    F. Y. Kwong and S. L. Buchwald, Org. Lett., 2003, 5, 793.Google Scholar
  10. 10.
    S. A. Galema, Chem. Soc. Rev., 1997, 26, 233.Google Scholar
  11. 11.
    R. S. Varma, Green Chem., 1999, 1, 43.Google Scholar
  12. 12.
    A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, and D. Mathe, Synthesis, 1998, 1213.Google Scholar
  13. 13.
    R. S. Varma, Pure Appl. Chem., 2001, 73, 193.Google Scholar
  14. 14.
    V. P. Ananikov and I. P. Beletskaya, Org. Biomol. Chem., 2004, 2, 284.Google Scholar
  15. 15.
    A. Ogawa, J.Organomet. Chem., 2000, 611, 463.Google Scholar
  16. 16.
    H. Kuniyasu, A. Ogawa, S.-I. Miyazaki, I. Ryu, N. Kambe, and N. Sonoda, J. Am. Chem. Soc., 1991, 113, 9796.Google Scholar
  17. 17.
    V. P. Ananikov, I. P. Beletskaya, G. G. Aleksandrov, and I. L. Eremenko, Organometallics, 2003, 22, 1414.Google Scholar
  18. 18.
    V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, G. G. Aleksandrov, and I. L. Eremenko, J. Organomet. Chem., 2003, 687, 451.Google Scholar
  19. 19.
    S. Dey, V. K. Jain, and B. Varghese, J. Organomet. Chem., 2001, 623, 48.Google Scholar
  20. 20.
    R. Oilunkaniemi, R. S. Laitinen, and M. Ahlgren, J. Organomet. Chem., 2001, 623, 168.Google Scholar
  21. 21.
    R. Oilunkaniemi, R. S. Laitinen, and M. Ahlgren,J. Organomet. Chem., 1999, 587, 200.Google Scholar
  22. 22.
    I. Nakanishi, S. Tanaka, K. Matsumoto, and S. Ooi, Acta Cryst. C, 1994, C50, 58.Google Scholar
  23. 23.
    M. S. Hannu-Kuure, K. Paldan, R. Oilunkaniemi, R. S. Laitinen, and M. Ahlgren, J. Organomet. Chem., 2003, 687, 538.Google Scholar
  24. 24.
    V. P. Ananikov and I. P. Beletskaya, Izv. Akad. Nauk, Ser. Khim., 2003, 771 [Russ. Chem. Bull., Int. Ed., 2003, 52, 811].Google Scholar
  25. 25.
    D. S. Pedersen and C. Rosenbohm, Synthesis, 2001, 2431.Google Scholar

Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • V. P. Ananikov
    • 1
  • I. P. Beletskaya
    • 2
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscowRussian Federation

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