Skip to main content
Log in

Pd-catalyzed oxidative olefination of arenes with olefins via C–H activation: Retention of the leaving group

  • Various Technological Processes
  • Published:
Russian Journal of Applied Chemistry Aims and scope Submit manuscript

Abstract

Pd-catalyzed direct oxidative olefination of arenes with olefins via C–H activation is described in the absence of any chelating directing groups. For Pd-catalyzed oxidative coupling between arenes and allyl acetate, it was observed the retention of the leaving group.

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. Beletskaya, I.P. and Cheprakov, A.V., Chem. Rev., 2000, vol. 100, pp. 3009.

    Article  CAS  Google Scholar 

  2. Meijere, A.D. and Meyer, F.E., Angew. Chem. Int. Ed., 1994, vol. 33, pp. 2379.

    Article  Google Scholar 

  3. Stephan, M.S.A., Teunissen, J.J.M., Verzijl, G.K.M., and De Vries, J.G., Angew. Chem., Int. Ed. Engl., 1998, vol. 37, pp. 662.

    Article  CAS  Google Scholar 

  4. Le Bras, J. and Muzart, J., Chem. Rev., 2011, vol. 111, pp. 1170.

    Article  CAS  Google Scholar 

  5. Patureau, F.W. and Glorius, F., J. Am. Chem. Soc., 2010, vol. 132, pp. 9982.

    Article  CAS  Google Scholar 

  6. Martinez, R., Chevalier, R., Darses, S., and Genet, J.-P., Angew. Chem. Int. Ed., 2006, vol. 45, pp. 8232.

    Article  CAS  Google Scholar 

  7. Wang, F., Song, G.-Y., and Li, X.-W., Org. Lett., 2010, vol. 12, pp. 5430.

    Article  CAS  Google Scholar 

  8. Ye, M.-C., Gao, G.-L., and Yu, J.-Q., J. Am. Chem. Soc., 2011, vol. 133, pp. 6964.

    Article  CAS  Google Scholar 

  9. Kubota, A., Emmert, M.H., and Sanford, M.S., Org. Lett., 2012, vol. 14, pp. 1760.

    Article  CAS  Google Scholar 

  10. Pan, D., Yu, M., Chen, W., and Jiao, N., Chem. Asian J., 2010, vol. 5, pp. 1090.

    Article  CAS  Google Scholar 

  11. Pankajakshan, S., Xu, Y.-H., Cheng, J.K., Low, M.T., and Loh, T.-P., Angew. Chem. Int. Ed., 2012, vol. 51, pp. 5701.

    Article  CAS  Google Scholar 

  12. Harada, S., Yano, H., and Obora, Y., Chem. Cat. Chem, 2013, vol. 5, pp. 121.

    CAS  Google Scholar 

  13. Yokota, T., Tani, M., Sakaguchi, S., and Ishii, Y., J. Am. Chem. Soc., 2005, vol. 125, pp. 1476.

    Article  Google Scholar 

  14. Tani, M., Sakaguchi, S., and Ishii, Y., J. Org. Chem., 2004, vol. 69, pp. 1221.

    Article  CAS  Google Scholar 

  15. Zheng, L. and Wang, J., Chem. Eur. J., 2012, vol. 18, pp. 9699.

    Article  CAS  Google Scholar 

  16. Feng, C., Feng, D., and Loh, T.-P., Org. Lett., 2013, vol. 15, pp. 3670.

    Article  CAS  Google Scholar 

  17. Mariamplillai, B., Herse, C., and Lautens, M., Org. Lett., 2005, vol. 7, pp. 4745.

    Article  Google Scholar 

  18. Zhang, Q. and Lu, X., J. Am. Chem. Soc., 2000, vol. 122, pp. 7604.

    Article  CAS  Google Scholar 

  19. Lautens, M., Tayama, E., and Herse, C., J. Am. Chem. Soc., 2005, vol. 127, pp. 72.

    Article  CAS  Google Scholar 

  20. Shang, X., Xiong, Y., Zhang, Y., Zhang, L., and Liu, Z., Synlett., 2012. vol. 259.

    Google Scholar 

  21. Li, Z., Zhang, Y., and Liu, Z.-Q., Org. Lett., 2012, vol. 14, pp. 74.

    Article  Google Scholar 

  22. Zhang, Y., Li, Z., and Liu, Z.-Q., Org. Lett., 2012, vol. 14, pp. 226.

    Article  CAS  Google Scholar 

  23. Kang, S.-K., Lee, H.-W., Jang, S.-B., Kim, T.H., and Pyun, S.-J., J. Org. Chem., 1996, vol. 61, pp. 2604.

    Article  CAS  Google Scholar 

  24. Beronocchi, E., Cacchi, S., Ciattini, P.G., and Morera Ortar, E.G., Tetrahedron Lett., 1992, vol. 33, pp. 3073.

    Article  Google Scholar 

  25. Ichihara, J., Chem. Commun., 1997. p. 1921.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jincheng Mao.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mao, J., Yang, X., Wang, D. et al. Pd-catalyzed oxidative olefination of arenes with olefins via C–H activation: Retention of the leaving group. Russ J Appl Chem 88, 2050–2055 (2015). https://doi.org/10.1134/S1070427215012023X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070427215012023X

Keywords

Navigation