Russian Journal of Organic Chemistry

, Volume 47, Issue 2, pp 230–235 | Cite as

N-heterocyclic carbenes: III. N-heterocyclic carbene ligands based on abietane in Suzuki-Miyaura reaction

  • V. A. Glushkov
  • M. S. Valieva
  • O. A. Maiorova
  • E. V. Baigacheva
  • A. A. Gorbunov


By reactions of N-alkyl- and N-arylimidazoles with methyl 12-bromoacetyldehydroabietate a series of unsymmetrically substituted chiral imidazolium bromides with the abietane fragment was synthesized. The salts obtained were suggested as new N-heterocyclic carbene ligands in the Suzuki-Miyaura reaction.


Hemihydrate Methoxycarbonyl Oxoethyl Imidazolium Salt Abietane 
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  1. 1.
    Glushkov, V.A. and Valieva, M.S., Tekhnicheskaya khimiya. Ot teorii k praktike. Sbornik, statei. II, Mezhdunarodnaya, konferentsiya (Technical Chemistry: from Theory to Practice. Collections of Papers. 2nd International Conference), Perm, 2010, vol. 1, p. 137.Google Scholar
  2. 2.
    Herrmann, W.A., Elison, M., Fisher, J., Köcher, C., and Artus, G.R.J., Angew. Chem., Int. Ed., 1995, vol. 34, p. 2371.CrossRefGoogle Scholar
  3. 3.
    Herrmann, W.A., Angew. Chem, Int. Ed., 2002, vol. 41, p. 1290.CrossRefGoogle Scholar
  4. 4.
    Kantchev, E.A.B., O’Brien, C.J., and Organ, M.G., Angew. Chem. Int. Ed., 2007, 46, 2768.CrossRefGoogle Scholar
  5. 5.
    Marion, N. and Nolan, S.P., Acc. Chem. Res., 2008, vol. 41, p. 1440; Selvakumar, K., Zapf, A., Spannenberg, A., and Beller, M., Chem. Eur. J., 2002, vol. 8, p. 3901; Organ, M.G., Chass, G.A., Fang, D.-C., Hopkinson, A.C., and Valente, C., Synthesis, 2008, vol. 17, p. 2776; Peh, G.-R., Kantchev, E.A.B., Er, J.-C., and Ying, J.Y., Chem. Eur. J., 2010, vol. 16, p. 4010.CrossRefGoogle Scholar
  6. 6.
    Hahn, F.E., Angew. Chem., Int. Ed., 2008, vol. 47, p. 3122; Jahnke, M.C. and Hahn, F.E., Top. Organometal. Chem., 2010, vol. 30, p. 95.CrossRefGoogle Scholar
  7. 7.
    Würtz, S. and Glorius, F., Acc. Chem. Res., 2008, vol. 41, p. 1523.CrossRefGoogle Scholar
  8. 8.
    Dowlut, M., Mallik, D., and Organ, M.G., Chem. Eur. J., 2010, vol. 16, p. 427.CrossRefGoogle Scholar
  9. 9.
    Lee, C.-C., Ke, W.-C., Chan, K.-T., Lai, C.-L., Hu, C.-H., and Lee, H.M., Chem. Eur. J., 2007, vol. 13, p. 582; Luan, X., Mariz, R., Gatti, M., Costabile, C., Poater, A., Cavallo, L., Linden, A., and Dorta, R., J. Am. Chem. Soc., 2008, vol. 130, p. 6848; Vieille-Petit, L., Clavier, H., Linden, A., Blumentritt, S., Nolan, S., and Dorta, R., Organometallics, 2010, vol. 29, p. 775.CrossRefGoogle Scholar
  10. 10.
    Alexander, S.G., Cole, M.L., and Morris, J.C., New J. Chem., 2009, vol. 33, p. 720.CrossRefGoogle Scholar
  11. 11.
    Ma, Y., Song, C., Jiang, W., Wu, Q., Wang, Y., Liu, X., and Andrus, M.B., Org. Lett., 2003, 5, 3317.CrossRefGoogle Scholar
  12. 12.
    Metallinos, C., Barrett, F.B., Wang, Y., Xu, S., and Tailor, N.J., Tetrahedron, 2006, vol. 62, 11145.CrossRefGoogle Scholar
  13. 13.
    Richter, H., Schwertfeger, H., Shreiner, P.R., Fröhlich, R., and Glorius, F., Synlett., 2009, p. 193.Google Scholar
  14. 14.
    Lee, S. and Hartwig, J.F, J. Org. Chem., 2001, vol. 66, p. 3402; Pernak, J., Feder-Kubis, J., Cieniecka-Rosłonkiewicz, A., Fischmeister, C., Griffin, S.T., Rogers, R.D. New, J. Chem., 2007, 31, 879; Würtz, S., Lohre, C., Fröhlich, R., Bergander, K., and Glorius, F., J. Am. Chem. Soc., 2009, vol. 131, p. 8344.CrossRefGoogle Scholar
  15. 15.
    Glushkov, V.A., Kotelev, M.S., Rudovskii, K.S., Maiorova, O.A., Tarantin, A.V., Tolstikov, A.G., Zh. Org. Khim., 2009, vol. 45, p. 416.Google Scholar
  16. 16.
    Irismetov, M.P., Tolstikov, G.A., Goryaev, M.I., and Von, G.P., Kaz. SSR, Gylym, Akad. Khabarlary, Izv. Akad. Nauk, Kaz.SSR, Ser. Khim., 1968, vol. 5, p. 85; Ref. Zh. Khim., 1969, 13Zh581.Google Scholar
  17. 17.
    Christmann, U. and Vilar, R., Angew. Chem. Int. Ed., 2005, vol. 44, p. 366; Marion, N., Navarro, O., Stevens, E.D., Ecarnot, E.C., Bell, A., Amoroso, D., and Nolan, S.P. Chem. Asian, J., 2010, vol. 5, p. 841.CrossRefGoogle Scholar
  18. 18.
    Gridnev, A.A. and Michaltseva, I.M. Synth. Commun., 1994, vol. 24, p. 1547.CrossRefGoogle Scholar
  19. 19.
    Occhipinti, G., Jensen, V.R., Törnroos, K.W., Frøystein, N.A., and Bjørsvik, H.-R., Tetrahedron, 2009, vol. 65, p. 7186.CrossRefGoogle Scholar
  20. 20.
    Collman, J.P. and Zhong, M., Org. Lett., 2000, vol. 2, p. 1233.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • V. A. Glushkov
    • 1
  • M. S. Valieva
    • 2
  • O. A. Maiorova
    • 1
  • E. V. Baigacheva
    • 1
  • A. A. Gorbunov
    • 1
  1. 1.Institute of Engineering Chemistry, Ural DivisionRussian Academy of SciencesPermRussia
  2. 2.Perm State UniversityPermRussia

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