Skip to main content
Log in

Cyclotrimerization of alkynes catalyzed by the naphthalene ruthenium complex [CpRu(C10H8)]+

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

The naphthalene ruthenium complex [CpRu(C10H8)]+ (in the presence of Cl ions) catalyzes the cyclotrimerization of 2,2-dimethyl-5,5-dipropargyl-1,3-dioxane-4,6-dione with alkynes (acetylene, hex-1-yne, hex-3-yne, oct-1-yne, phenylacetylene, trimetylsilylacetylene, octa-1,7-diyne, pent-1-yn-5-ol, methyl propargyl ether, and propargyl acetate) giving tricyclic aromatic compounds in 55–85% yields.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. Saito, Y. Yamamoto, Chem. Rev., 2000, 100, 2901.

    Article  CAS  Google Scholar 

  2. Y. Yamamoto, Curr. Org. Chem., 2005, 9, 503.

    Article  CAS  Google Scholar 

  3. P. R. Chopadea, J. Louie, Adv. Synth. Catal., 2006, 348, 2307.

    Article  Google Scholar 

  4. Y. Yamamoto, J. Ishii, H. Nishiyama, K. Itoh, J. Am. Chem. Soc., 2005, 127, 9625.

    Article  CAS  Google Scholar 

  5. K. C. Nicolaou, Y. Tang, J. Wang, Angew. Chem., Int. Ed., 2009, 48, 3449.

    Article  CAS  Google Scholar 

  6. Y. Zou, A. Deiters, J. Org. Chem., 2010, 75, 5355.

    Article  CAS  Google Scholar 

  7. X. Bugaut, X. Guinchard, E. Roulland, J. Org. Chem., 2010, 75, 8190

    Article  CAS  Google Scholar 

  8. P. Novák, R. Pohl, M. Kotora, M. Hocek, Org. Lett., 2006, 8, 2051.

    Article  Google Scholar 

  9. G. T. Shchetnikov, S. N. Osipov, C. Bruneau, P. H. Dixneuf, Synlett, 2008, 578.

  10. Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143.

    Article  CAS  Google Scholar 

  11. R. Schmid, K. Kirchner, Eur. J. Inorg. Chem., 2004, 2609.

  12. J. A. Varela, C. Saá, J. Organomet. Chem., 2009, 694, 143.

    Article  CAS  Google Scholar 

  13. Y. Yamamoto, K. Yamashita, Y. Harada, Chem. Asian J., 2010, 5, 946.

    Article  CAS  Google Scholar 

  14. E. E. Karslyan, A. I. Konovalov, D. S. Perekalin, P. V. Petrovskii, A. R. Kudinov, Izv. Akad. Nauk, Ser. Khim., 2008, 1997 [Russ. Chem. Bull., Int. Ed., 2008, 57, 2032].

  15. D. S. Perekalin, E. A. Trifonova, I. V. Glukhov, J. Holub, A. R. Kudinov, Czech. Coll. Chem. Commun., 2010, 75, 1139.

    Article  CAS  Google Scholar 

  16. E. E. Karslyan, D. S. Perekalin, P. V. Petrovskii, K. A. Lyssenko, A. R. Kudinov, Izv. Akad. Nauk, Ser. Khim., 2008, 2158 [Russ. Chem. Bull., Int. Ed., 2008, 57, 2201].

    Google Scholar 

  17. E. E. Karslyan, D. S. Perekalin, P. V. Petrovskii, A. O. Borisova, A. R. Kudinov, Izv. Akad. Nauk, Ser. Khim., 2009, 572 [Russ. Chem. Bull., Int. Ed., 2009, 58, 585].

    Google Scholar 

  18. D. S. Perekalin, E. E. Karslyan, P. V. Petrovskii, Y. V. Nelyubina, K. A. Lyssenko, A. S. Kononikhin, E. N. Nikolaev, A. R. Kudinov, Chem. Eur. J., 2010, 16, 8466.

    Article  CAS  Google Scholar 

  19. D. S. Perekalin, E. E. Karslyan, A. O. Borissova, A. R. Kudinov, Mendeleev. Commun., 2011, 21, 82.

    Article  CAS  Google Scholar 

  20. L. Hintermann, T. T. Dang, A. Labonne, T. Kribber, L. Xiao, P. Naumov, Chem. Eur. J., 2009, 15, 7167 and references cited herein.

    Article  CAS  Google Scholar 

  21. D. Linder, F. Buron, S. Constant, J. Lacour, Eur. J. Org. Chem., 2008, 5778 and references cited herein.

  22. Y. Yamamoto, H. Kitahara, R. Ogawa, H. Kawaguchi, K. Tatsumi, K. Itoh, J. Am. Chem. Soc., 2000, 122, 4310.

    Article  CAS  Google Scholar 

  23. K. Kirchner, M. J. Calhorda, R. Schmid, L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721.

    Article  CAS  Google Scholar 

  24. J. A. Varela, C. Saá, J. Organomet. Chem., 2009, 694, 143.

    Article  CAS  Google Scholar 

  25. K. Tanaka, K. Toyoda, A. Wada, K. Shirasaka, M. Hirano, Chem. Eur. J., 2005, 11, 1145.

    Article  CAS  Google Scholar 

  26. S. Kezuka, S. Tanaka, T. Ohe, Y. Nakaya, R. Takeuchi, J. Org. Chem., 2006, 71, 543.

    Article  CAS  Google Scholar 

  27. E. P. Kündig, F. R. Monnier, Adv. Synth. Catal., 2004, 346, 901.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. R. Kudinov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2073–2076, October, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Perekalin, D.S., Trifonova, E.A., Petrovskii, P.V. et al. Cyclotrimerization of alkynes catalyzed by the naphthalene ruthenium complex [CpRu(C10H8)]+ . Russ Chem Bull 60, 2110–2113 (2011). https://doi.org/10.1007/s11172-011-0324-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-011-0324-3

Key words

Navigation