Skip to main content
Log in

Copper(I)-catalyzed amination of halothiophenes with polyamines

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Copper(I)-catalyzed hetarylation of a series of polyamines and of 4,7,10-trioxatridecane-1,13-diamine with halothiophenes has been studied with a view to obtaining the corresponding N,N′-dihetaryl derivatives. The target products can be obtained using both 3-iodothiophene in the presence of CuI/L-proline/EtCN or CuI/N,N-dimethylglycine/EtCN as catalytic system and 3-bromothiophene in the system CuI/2-(2-methyl-1-oxopropyl)cyclohexanone/DMF. The latter system is also suitable for the hetarylation of 4,7,10-trioxatridecane-1,13-diamine with 3-iodothiophene. In some cases, N-(thiophen-3-yl) derivatives have also been isolated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Wuerthner, F., Yao, S., Debaerdemaeker, T., and Wortmann, R., J. Am. Chem. Soc., 2002, vol. 124, p. 9431.

    Article  CAS  Google Scholar 

  2. Kiryanov, A.A., Seed, A.J., and Sampson, P., Tetrahedron Lett., 2001, vol. 42, p. 8797.

    Article  CAS  Google Scholar 

  3. Jen, A.K.Y., Rao, V.P., Wong, K.Y., and Drost, K.J., J. Chem. Soc., Chem. Commun., 1993, p. 90.

    Google Scholar 

  4. Heyde, C., Zug, I., and Hartmann, H., Eur. J. Org. Chem., 2000, p. 3273.

    Google Scholar 

  5. Norris, R.K., Chemistry of Heterocyclic Compounds, Gronowitz, S., Ed., New York: Wiley, 1986, vol. 44, part 2, p. 631.

  6. Reinicke, M.G. and Adickes, H.W., J. Am. Chem. Soc., 1968, vol. 90, p. 511.

    Article  Google Scholar 

  7. Prim, D. and Kirsch, G., Tetrahderon, 1999, vol. 55, p. 6511.

    Article  CAS  Google Scholar 

  8. Hartmann, H. and Scheithauer, S., J. Prakt. Chem., 1969, vol. 311, p. 827.

    Article  CAS  Google Scholar 

  9. Bernardi, P., Dembech, P., Fabbri, G., Ricci, A., and Secomi, G., J. Org. Chem., 1999, vol. 64, p. 641.

    Article  CAS  Google Scholar 

  10. Cané, F., Brancaleoni, D., Dembech, P., Ricci, A., and Seconi, G., Synthesis, 1997, p. 545.

    Google Scholar 

  11. Watanabe, M., Yamamoto, T., and Nishiyama, M., Chem. Commun., 2000, p. 133.

    Google Scholar 

  12. Hooper, M.W., Utsunomiya, M., and Hartwig, J.F., J. Org. Chem., 2003, vol. 68, p. 2861.

    Article  CAS  Google Scholar 

  13. Ogawa, K., Radke, K.R., Rothstein, S.D., and Rasmussen, S.C., J. Org. Chem., 2001, vol. 66, p. 9067.

    Article  CAS  Google Scholar 

  14. Luker, T.J., Beaton, H.G., Whiting, M., Mete, A., and Cheshire, D.R., Tetrahedron Lett., 2000, vol. 41, p. 7731.

    Article  CAS  Google Scholar 

  15. Lu, Zh., Twieg, R.J., and Huang, S.D., Tetrahedron Lett., 2003, vol. 44, p. 6289.

    Article  CAS  Google Scholar 

  16. Lu, Zh. and Twieg, R.J., Tetrahedron, 2005, vol. 61, p. 903.

    Article  CAS  Google Scholar 

  17. Tang, B.-X., Guo, Sh.-M., Zhang, M.-B., and Li, J.-H., Synthesis, 2008, p. 1707.

    Google Scholar 

  18. Kwong, F.Y. and Buchwald, S.L., Org. Lett., 2003, vol. 5, p. 793.

    Article  CAS  Google Scholar 

  19. Anokhin, M.V., Averin, A.D., and Beletskaya, I.P., Eur. J. Org. Chem., 2011, p. 6240.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. P. Beletskaya.

Additional information

Original Russian Text © M.V. Anokhin, A.D. Averin, S.P. Panchenko, O.A. Maloshitskaya, I.P. Beletskaya, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 7, pp. 943–947.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Anokhin, M.V., Averin, A.D., Panchenko, S.P. et al. Copper(I)-catalyzed amination of halothiophenes with polyamines. Russ J Org Chem 50, 923–927 (2014). https://doi.org/10.1134/S107042801407001X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801407001X

Keywords

Navigation