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Allylic alkylation of benzoimidazole catalyzed by palladium complexes

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Bis(dibenzylidenacetone)palladium is an efficient and highly selective catalyst for the formation ofN-(2,7-dimethylocta-2,7-dienyl)benzoimidazole in the allylation of benzoimidazole withN-(2,7-dimethylocta-2,7-dienyl)-N-methylpiperidinium iodide in the presence of NaH.

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References

  1. E. Kuwano, N. Sato, and M. Eto,Agr. Biol. Chem., 1982,46, 1715.

    CAS  Google Scholar 

  2. E. Kuwano, R. Takeda, and M. Eto,Agr. Biol. Chem., 1985,49, 483.

    CAS  Google Scholar 

  3. M. Häring,Helv. Chim. Acta, 1959,42, 1845.

    Article  Google Scholar 

  4. L. J. Mathias and D. Burkett,Tetrahedron Lett., 1979, 4709.

  5. Y. Kikugawa,Synthesis, 1981, 124.

  6. UK Pat., 1960, 849, 793;Chem Abstrs., 1963,59, 7535d.

  7. USA Pat. 1952, 2, 623, 879;Chem. Abstrs., 1953,47, 9367c.

  8. E. A. Savill-Stones, S. D. Lindell, N. S. Jennings, J. C. Head, and M. J. Ford,J. Chem. Soc., Perkin Trans. 1, 1991, 2603.

  9. L. L. Gundersen, T. Benneche, and K. Undheim,Tetrahedron Lett., 1992,33, 1085.

    Article  CAS  Google Scholar 

  10. C. T. Evans, S. M. Roberts, K. A. Shobern, and A. G. Sutherlend,J. Chem. Soc., Perkin Trans. 1, 1992, 589.

  11. R. A. Mackeith, R. McCague, H. F. Olivo, C. F. Palmer, and S. M. Roberts,J. Chem. Soc., Perkin Trans. 1, 1993, 313.

  12. S. M. Roberts and K. A. Shobern,J. Chem. Soc., Perkin Trans. 1, 1991, 2605.

  13. L. L. Gundersen, T. Benneche, F. Rise, A. Gogolc, and K. Undheim,Acta Chem. Scand., 1992,46 (8), 761.

    CAS  Google Scholar 

  14. F. Liotta, C. R. Unelius, J. Kozak, and T. Norin,Acta Chem. Scand., 1992,46, 686.

    Article  CAS  Google Scholar 

  15. V. Bolit, B. Chaguir, and D. Sinou,Tetrahedron Lett., 1992,33, 2481.

    Article  Google Scholar 

  16. B. M. Trost, G. H. Kuo, and T. Benneche,J. Am. Chem. Soc., 1988,110, 621.

    Article  CAS  Google Scholar 

  17. K. E. Atkis, W. E. Walker, and R. M. Manyik,Tetrahedron Lett., 1970, 3821.

  18. K. Takahashi, G. Hata, and A. Miyake,Bull. Chem. Soc. Jpn., 1972,45, 230.

    Article  CAS  Google Scholar 

  19. E. A. Petrushkina and L. I. Zakharkin,Izv. Akad. Nauk, Ser. Khim., 1994, 270 [Russ. Chem. Bull., 1994,43, 249 (Engl. Transl.)].

    Google Scholar 

  20. L. I. Zakharkin, E. A. Petrushkina, and L. S. Podvisotskaya,Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 886 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983,32, 805 (Engl. Transl.)].

    Google Scholar 

  21. L. I. Zakharkin and E. A. Petrushkina,Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1344 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986,35, 1219 (Engl. Transl.)].

  22. E. A. Petrushkina and V. I. Bregadze,Metalloorg. Khim., 1992,5, 1161 [Organomet. Chem. (USSR), 1992,5, 567 (Engl. Transl.)].

    CAS  Google Scholar 

  23. B. M. Trost and T. R. Verhoeven,J. Am. Chem. Soc., 1980,102, 4730.

    Article  CAS  Google Scholar 

  24. L. C. Satek, S. O. Grim, and P. R. Coulson,Inorg. Synth., 1972,13, 121.

    Google Scholar 

  25. Y. Takahashi, T. Ito, S. Sakai, and Y. Ishii,Chem. Commun., 1970, 1065.

  26. E. A. Petrushkina, V. V. Gavrilenko, Yu. F. Oprunenko, and N. G. Akhmedov,Zh. Obshch. Khim., 1996,66, 1864 [J. Gen. Chem., 1996,66 (Engl. Transl.)].

    CAS  Google Scholar 

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 357–360, February, 1999.

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Petrushkina, E.A., Polonik, N.B. Allylic alkylation of benzoimidazole catalyzed by palladium complexes. Russ Chem Bull 48, 356–358 (1999). https://doi.org/10.1007/BF02494564

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  • DOI: https://doi.org/10.1007/BF02494564

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