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Arylation of heterocycles in the reaction of heterocyclic mercury derivatives in the presence of palladium complexes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A convenient method is proposed for the synthesis of aryl derivatives of heterocyclic compounds by the coupling reaction of heterocyclic mercury derivatives and tin derivatives with aryl and heteryl iodides in the presence of palladium complexes. In the case of organotin compounds, the reaction proceeds without the formation of side-products although mercury derivatives are usually more available.

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Literature cited

  1. W. E. Bachmann and R. A. Hofmann, in: Organic Reactions [Russian translation], Collection 2, Izd. Inostr. Lit., Moscow (1950), p. 244.

    Google Scholar 

  2. M. Kumada, Pure Appl. Chem., 52, 669 (1980).

    Google Scholar 

  3. L. N. Pridgen, J. Heterocycl. Chem., 12, 443 (1975).

    Google Scholar 

  4. K. Tamao, S. Kodama, I. Nakajima, T. Nokatsuka, A. Minato, and M. Kumada, Heterocycles, 3, 1133 (1975).

    Google Scholar 

  5. E. D. Thorsett and F. R. Stermitz, J. Heterocycl. Chem., 10, 243 (1973).

    Google Scholar 

  6. A. Minato, K. Tamao, T. Hayashi, K. Suzuki, and M. Kumada, Tetrahedron Lett., 22, 5319 (1981).

    Google Scholar 

  7. A. K. Kashin, I. G. Bumagina, N. A. Bumagin, and I. P. Beletskaya, Zh. Org. Khim., 17, 21 (1981).

    Google Scholar 

  8. N. A. Bumagin, I. O. Kalinovskii, and I. P. Beletskaya, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2431 (1981).

    Google Scholar 

  9. K. Takagi, N. Hayama, T. Okamoto, Y. Sakakibara, and S. Oka, Bull. Chem. Soc. Jpn., 50, 2741 (1977).

    Google Scholar 

  10. H. Wynberg, T. J. Van Bergen, and R. M. Kellog, J. Org. Chem., 34, 3176 (1969).

    Google Scholar 

  11. H.-S. Ryang and U. Sakurai, Chem. Commun., No. 10, 594 (1972).

    Google Scholar 

  12. A. G. Makarova and A. N. Nesmeyanov, Methods in Heteroorganic Chemistry, Mercury [in Russian], Izd. Nauka, Moscow (1965), p. 101.

    Google Scholar 

  13. J. R. Pratt, F. H. Pinkerton, and S. F. Thames, J. Organomet. Chem., 38, 29 (1972).

    Google Scholar 

  14. P. Fitton and E. A. Rick, J. Organomet. Chem., 28, 287 (1971).

    Google Scholar 

  15. A. O. King and E. Negishi, J. Org. Chem., 43, 358 (1978).

    Google Scholar 

  16. J. P. Haudegond, Y. Chauvin, and D. Commereuc, J. Org. Chem., 44, 3063 (1979).

    Google Scholar 

  17. R. Linsted, J. Elvidge, M. Wally, and J. Wilkinson, Modern Research Methods in Organic Chemistry [Russian translation], Izd. Inostr. Lit., Moscow (1959), p. 279.

    Google Scholar 

  18. K. Kindler, Ann. Chem., 450, 1 (1926).

    Google Scholar 

  19. G. E. K. Branch and A. C. Nixon, J. Am. Chem. Soc., 58, 2499 (1936).

    Google Scholar 

  20. K. Takagi, N. Hayama, and T. Okamoto, Chem. Lett., No. 2, 191 (1978).

    Google Scholar 

  21. A. Binz and C. Rath, Ann. Chem., 486, 101 (1931).

    Google Scholar 

  22. E. Gergely and T. Iredale, J. Chem. Soc., No. 10, 3226 (1953).

    Google Scholar 

  23. A. W. Johnson, J. Chem. Soc., No. 3, 895 (1946).

    Google Scholar 

  24. F. Friquelli, G. Marino, and A. Taticchi, J. Chem. Soc. Perkin Trans. II, No. 2, 158 (1972).

    Google Scholar 

  25. M. Nilsson and C. Ullenius, Acta. Chem. Scand., 24, 2379 (1970).

    Google Scholar 

  26. Farbwerke Hoechst AG, Netherlands Patent No. 6,611,004 (1967); Chem. Abstr., 67, 33840 (1967).

    Google Scholar 

  27. L. Fisera, J. Kovac, and E. Komanova, Chem. Zvesti, 30, 499 (1976).

    Google Scholar 

  28. H. Rappoport, M. Look, and G. J. Kelly, J. Am. Chem. Soc., 74, 6293 (1952).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1467–1470, November, 1983.

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Bumagin, N.A., Kalinovskii, I.O. & Beletskaya, I.P. Arylation of heterocycles in the reaction of heterocyclic mercury derivatives in the presence of palladium complexes. Chem Heterocycl Compd 19, 1159–1162 (1983). https://doi.org/10.1007/BF00515346

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  • DOI: https://doi.org/10.1007/BF00515346

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