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Nonconventional allylation of norbornene and norbornadiene derivatives: stoichiometry and catalysis

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Abstract

The key trends for the development of catalytic reactions of allyllic esters of carboxylic acids with norbornene, norbornadiene, and their heterocyclic analogs in the presence of the nickel and palladium complexes are discussed. The main approaches to investigation of the mechanism using model stoichiometric reactions and quantum chemical calculations are described.

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References

  1. M. Catellani, G. P. Chiusoli, E. Dradi, G. Salerno, J. Organomet. Chem., 1979, 177, C29.

    Article  CAS  Google Scholar 

  2. R. P. Hughes, J. Powell, J. Organomet. Chem., 1971, 30, C45.

    Article  CAS  Google Scholar 

  3. M. C. Gallazzi, L. Porrim, G. Vitulli, J. Organomet. Chem., 1975, 97, 131.

    Article  CAS  Google Scholar 

  4. W. Oppolzer, in Comprehensive Organometallic Chemistry II, Eds E. W. Abel, F. G. A. Stone, G. Wilkinson, Pergamon Press, Oxford, UK, 1995, Vol. 9, p. 905.

    Google Scholar 

  5. J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, John Wiley and Sons, Chichester, 1995.

    Google Scholar 

  6. W. Oppolzer, Pure Appl. Chem., 1990, 62, 1941.

    Article  CAS  Google Scholar 

  7. E. M. Evstigneeva, R. S. Shamsiev, V. R. Flid, Vestn. MITKhT [Bulletin of Moscow Institute of Fine Chemical Technology], 2006, 1, No. 3, 3 (in Russian).

    Google Scholar 

  8. M. Catellani, E. Motti, F. Faccini, R. Ferraccioli, Pure Appl. Chem., 2005, 77, No. 7, 243.

    Article  Google Scholar 

  9. V. R. Flid, O. S. Manulik, A. P. Belov, A. A. Grigor’ev, Metalloorg. Khim., 1991, 4, 864 [Organomet. Chem., 1991, 4 (Engl. Transl.).

    CAS  Google Scholar 

  10. U. M. Dzhemilev, R. I. Khusnutdinov, D. K. Galeev, O. M. Nefedov, G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 138 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 122 (Engl. Transl.)].

  11. U. M. Dzhemilev, R. I. Khusnutdinov, D. K. Galeev, G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 154 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 137 (Engl. Transl.)].

    Google Scholar 

  12. V. R. Flid, O. S. Manulik, D. V. Dmitriev, V. B. Kouznetsov, E. M. Evstigneeva, A. P. Belov, A. A. Grigor’ev, Eurasian ChemTech J., 2001, 3, 201.

    Google Scholar 

  13. V. R. Flid, Yu. G. Shestakova, E. A. Katsman, Kinet. Katal., 1992, 33, 223 [Kinet. Catal., 1992, 33 (Engl. Transl.).

    Google Scholar 

  14. Pat. RF No. 1 796 605; Byul. Izobret. [Invention Bulletin], 1993, No. 7, p. 76 (in Russian).

  15. Pat. RF No. 1 796 606; Byul. Izobret. [Invention Bulletin], 1993, No. 7, p. 76 (in Russian).

  16. Pat. RF No. 1 796 608; Byul. Izobret. [Invention Bulletin], 1993, No. 7, p. 77 (in Russian).

  17. Author’s Certificate. 1 148 269 USSR; Byul. Izobret. [Invention Bulletin], 1984, No. 3, p. 38 (in Russian).

  18. N. Tsukada, T. Sato, Y. Inoue, Tetrahedron Lett., 2000, 41, 4181.

    Article  CAS  Google Scholar 

  19. E. M. Evstigneeva, O. S. Manulik, V. R. Flid, Kinet. Katal., 2004, 45, 188 [Kinet. Catal., 2004, 45, 172 (Engl. Transl.)].

    Article  Google Scholar 

  20. E. M. Evstigneeva, O. S. Manulik, V. R. Flid, I. P. Stolyarov, N. Yu. Kozitsina, M. N. Vargaftik, I. I. Moiseev, Izv. Akad. Nauk, Ser. Khim., 2004, 1292 [Russ. Chem. Bull., Int. Ed., 2004, 53, 1345].

    Google Scholar 

  21. S. Gao, H. Zhang, X. Wang, X. Wang, W. Mai, C. Peng, L. Ge, Nanotechnology, 2005, 16, 1234.

    Article  CAS  Google Scholar 

  22. S. V. Leont’eva, O. S. Manulik, E. M. Evstigneeva, E. N. Bobkova, V. R. Flid, Kinet. Katal., 2006, 47, 391 [Kinet. Catal., 2006, 47, 172 (Engl. Transl.)].

    Google Scholar 

  23. T. Satoh, M. Miura, Top. Organomet. Chem., 2005, 14, 1.

    CAS  Google Scholar 

  24. I. P. Stolyarov, A. E. Gekhman, I. I. Moiseev, A. Yu. Kolesnikov, E. M. Evstigneeva, V. R. Flid, Izv. Akad. Nauk, Ser. Khim., 2007, 309 [Russ. Chem. Bull., Int. Ed., 2007, 56, 320].

    Google Scholar 

  25. D. J. Gárdenas, M. Alcamí, M. Méndez, A. M. Echavarren, Chem. Eur. J., 2003, 9, 96.

    Article  Google Scholar 

  26. E. Gomez-Bengoa, J. M. Cuerva, A. M. Echavarren, G. Martorell, Angew. Chem., Int. Ed. Engl., 1997, 36, 767.

    Article  CAS  Google Scholar 

  27. D. J. Cárdenas, A. M. Echavarren, New J. Chem., 2004, 28, 338.

    Article  Google Scholar 

  28. M. Garsía-Iglesias, E. Buñuel, D. J. Cárdenas, Organometallics, 2006, 25, 3620.

    Google Scholar 

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Correspondence to V. R. Flid.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 823–830, April, 2008.

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Evstigneeva, E.M., Flid, V.R. Nonconventional allylation of norbornene and norbornadiene derivatives: stoichiometry and catalysis. Russ Chem Bull 57, 837–844 (2008). https://doi.org/10.1007/s11172-008-0121-9

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  • DOI: https://doi.org/10.1007/s11172-008-0121-9

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