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Synthesis and transformations of metallacycles 38. The Cp2ZrCl2-catalyzed cyclometallation of α,ω-diynes upon the action of RMgR’ or R n AlCl3−n

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Abstract

The Cp2ZrCl2-catalyzed cyclometallation of α,ω-alkadiynes upon the action of RMgR’ or R n AlCl3−n was accomplished to yield unsaturated di- and tricyclic (magnesa)aluminacarbocycles in up to 85% yield.

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References

  1. V. A. D’yakonov, O. A. Trapeznikova, U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 2011, 103 [Russ. Chem. Bull., Int. Ed., 2011, 60, 107].

    Google Scholar 

  2. U. M. Dzhemilev, A. G. Ibragimov, A. P. Zolotarev, Mendeleev Commun., 1992, 135.

  3. V. A. D’yakonov, R. A. Tuktarova, O. A. Trapeznikova, N. R. Popod’ko, L. M. Khalilov, ARKIVOC, 2011, viii, 20.

    Google Scholar 

  4. U. M. Dzhemilev, A. G. Ibragimov, I. R. Ramazanov, M. P. Luk’yanova, A. Z. Sharipova, Izv. Akad. Nauk, Ser. Khim., 2001, 465 [Russ. Chem. Bull., Int. Ed., 2001, 50, 484].

    Google Scholar 

  5. V. A. D’yakonov, L. F. Galimova, A. G. Ibragimov, U. M. Dzhemilev, Zh. Org. Khim., 2008, 44, 1308 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44, 1291].

    Google Scholar 

  6. V. A. D’yakonov, R. A. Zinnurova, A. G. Ibragimov, U. M. Dzhemilev, Zh. Org. Khim., 2007, 43, 184 [Russ. J. Org. Chem. (Engl. Transl.), 2007, 43, 176].

    Google Scholar 

  7. U. M. Dzhemilev, Mendeleev Commun., 2008, 18, 1.

    Article  CAS  Google Scholar 

  8. E. Negishi, J.-L. Montchamp, L. Anastasia, A. Elizarov, D. Choueiry, Tetrahedron Lett., 1998, 39, 2503.

    Article  CAS  Google Scholar 

  9. U. M. Dzhemilev, A. G. Ibragimov, I. R. Ramazanov, M. P. Luk’yanova, A. Z. Sharipova, L. M. Khalilov, Izv. Akad. Nauk, Ser. Khim., 2000, 1092 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1086].

    Google Scholar 

  10. V. A. D’yakonov, A. G. Ibragimov, L. M. Khalilov, A. A. Makarov, R. K. Timerkhanov, R. A. Tuktarova, L. F. Galimova, Khim. Geterotsikl. Soedin., 2009, 393 [Chem. Heterocycl. Compd. (Engl. Transl.), 2009, 45].

  11. V. A. D’yakonov, in Organometallic Compounds: Preparation, Structure and Properties, Ed. H. F. Chin, NOVA Sci. Publ., New York, 2010, 49.

    Google Scholar 

  12. Z. Xi, P. Li, Angew. Chem., Int. Ed., 2000, 39, 2950.

    Article  CAS  Google Scholar 

  13. U. M. Dzhemilev, A. G. Ibragimov, J. Organomet. Chem., 2010, 695, 1085.

    Article  CAS  Google Scholar 

  14. V. A. D’yakonov, Dzhemilev Reactions in Organic and Organometallic Synthesis, NOVA Sci. Publ., New York, 2010, 96.

    Google Scholar 

  15. V. A. D’yakonov, A. A. Makarov, U. M. Dzhemilev, Tetrahedron, 2010, 66, 6885.

    Article  Google Scholar 

  16. U. M. Dzhemilev, A. G. Ibragimov, Usp. Khim., 2000, 69, 134 [Russ. Chem. Rev. (Engl. Transl.), 2000, 69].

    Google Scholar 

  17. U. M. Dzhemilev, Tetrahedron, 1995, 51, 4333.

    Article  CAS  Google Scholar 

  18. D. Y. Kondakov, E. Negishi, J. Am. Chem. Soc., 1996, 118, 1577.

    Article  CAS  Google Scholar 

  19. D. P. Lewis, R. J. Whitby, R. V. H. Jones, Tetrahedron, 1995, 51, 4541.

    Article  CAS  Google Scholar 

  20. V. A. D’yakonov, R. K. Timerkhanov, T. V. Tumkina, A. G. Ibragimov, U. M. Dzhemilev, Tetrahedron Lett., 2009, 50, 1270.

    Article  Google Scholar 

  21. V. A. D’yakonov, E. Sh. Finkelshtein, A. G. Ibragimov, Tetrahedron Lett., 2007, 48, 8583.

    Article  Google Scholar 

  22. U. M. Dzhemilev, V. A. D’yakonov, L. O. Khafizova, A. G. Ibragimov, Tetrahedron, 2004, 60, 1287.

    Article  CAS  Google Scholar 

  23. V. A. D’yakonov, R. K. Timerkhanov, U. M. Dzhemilev, A. G. Ibragimov, Izv. Akad. Nauk, Ser. Khim., 2007, 2156 [Russ. Chem. Bull., Int. Ed., 2007, 56, 2232].

    Google Scholar 

  24. E. Negishi, S. Huo, in Titanium and Zirconium in Organic Synthesis, Ed. I. Marek, Willey-VCH, New York, 2002, 32.

    Google Scholar 

  25. T. Takahashi, F.-Y. Tsai, Y. Li, K. Nakajima, M. Kotora, J. Am. Chem. Soc., 1999, 121, 11093.

    Article  CAS  Google Scholar 

  26. E. Negishi, D. Y. Kondakov, D. Choueiry, K. Kasai, T. Takahashi, J. Am. Chem. Soc., 1996, 118, 9577.

    Article  CAS  Google Scholar 

  27. E. Negishi, F. E. Cederbaum, T. Takahashi, Tetrahedron Lett., 1986, 27, 2829.

    Article  CAS  Google Scholar 

  28. E. Negishi, D. R. Swanson, F. E. Cederbaum, T. Takahashi, Tetrahedron Lett., 1987, 28, 917.

    Article  CAS  Google Scholar 

  29. G. Agnel, E. Negishi, J. Am. Chem. Soc., 1991, 113, 7424.

    Article  CAS  Google Scholar 

  30. E. Negishi, T. Takahashi, Bull. Chem. Soc. Jpn, 1998, 71, 755.

    Article  CAS  Google Scholar 

  31. R. Kh. Freidlina, E. M. Brainina, A. N. Nesmeyanov, Dokl. Akad. Nauk SSSR, 1969, 138, 1369 [Dokl. Chem. (Engl. Transl.), 1969].

    Google Scholar 

  32. T. Takahashi, S. Li, W. Huang, F. Kong, K. Nakajima, B. Shen, T. Ohe, K. Kanno, J. Org. Chem., 2006, 71, 7967.

    Article  CAS  Google Scholar 

  33. T. Takahashi, M. Kitamura, B. Shen, K. Nakajima, J. Am. Chem. Soc., 2000, 122, 12876.

    Article  CAS  Google Scholar 

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Correspondence to V. A. D’yakonov.

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For Part 37, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1607–1613, August, 2011.

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D’yakonov, V.A., Tuktarova, R.A. & Dzhemilev, U.M. Synthesis and transformations of metallacycles 38. The Cp2ZrCl2-catalyzed cyclometallation of α,ω-diynes upon the action of RMgR’ or R n AlCl3−n . Russ Chem Bull 60, 1633–1639 (2011). https://doi.org/10.1007/s11172-011-0244-2

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  • DOI: https://doi.org/10.1007/s11172-011-0244-2

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