Skip to main content
Log in

Highly Active Pd-PEPPSI Complexes for Suzuki-Miyaura Cross-coupling of Aryl Chlorides: an Investigation on the Effect of Electronic Properties

  • Article
  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

Three new Pd-pyridine enhanced precatalyst preparation stabilization and initiation(PEPPSI) complexes with halogen groups on the N-heterocyclic carbene and pyridine were prepared. Their structures have been clearly characterized by nuclear magnetic resonance spectroscopy and X-ray single-crystal diffraction. The effects of the electronic properties of halogen groups on the catalytic activity in the Suzuki-Miyaura cross-coupling of aryl chlorides were investigated. These Pd-PEPPSI complexes could catalyze the cross-coupling reaction efficiently with a low catalyst loading(0.05%, molar ratio) at room temperature and the products were obtained in high yields.

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. Negishi E. I., de Meijere A., Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, Inc., New York., 2002

    Book  Google Scholar 

  2. de Meijere A., Diederich F., Metal-catalyzed Cross-coupling Reactions, 2nd Edition, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2014

    Book  Google Scholar 

  3. Arduengo A. J., Harlow R. L., Kline M., J. Am. Chem. Soc., 1991, 113(1), 361

    Article  CAS  Google Scholar 

  4. Fantasia S., Petersen J. L., Jacobsen H., Cavallo L., Nolan S. P., Organometallics, 2007, 26(24), 5880

    Article  CAS  Google Scholar 

  5. Jones W. D., J. Am. Chem. Soc., 2009, 131(42), 15075

    Article  CAS  Google Scholar 

  6. Hopkinson M. N., Richter C., Schedler M., Glorius F., Nature, 2014, 510, 485

    Article  CAS  Google Scholar 

  7. Vummaleti S. V. C., Nelson D. J., Poater A., Adrián G. S., Cordes D. B., Slawin A. M. Z., Nolan S. P., Cavallo L., Chemical Science, 2015, 6, 1895

    Article  CAS  Google Scholar 

  8. Kantchev E. A., O’Brien C. J., Organ M. G., Angew. Chem., Int. Ed., 2007, 46(16), 2768

    Article  CAS  Google Scholar 

  9. Würtz S., Glorius F., Acc. Chem. Res., 2008, 41(11), 1523

    Article  Google Scholar 

  10. Fortman G. C., Nolan S. P., Chem. Soc. Rev., 2011, 40(10), 5151

    Article  CAS  Google Scholar 

  11. Froese R. D. J., Lombardi C., Pompeo M., Rucker R. P., Organ M. G., Acc. Chem. Res., 2017, 50(9), 2244

    Article  CAS  Google Scholar 

  12. Li G., Shi S., Lei P., Szostak M., Advanced Synthesis & Catalysis, 2018, 360(7), 1538

    Article  CAS  Google Scholar 

  13. Marion N., Nolan S. P., Acc. Chem. Res., 2008, 41(11), 1440

    Article  CAS  Google Scholar 

  14. Calimsiz S., Sayah M., Mallik D., Organ M. G., Angew. Chem., Int. Ed., 2010, 49(11), 2014

    Article  CAS  Google Scholar 

  15. Valente C., Calimsiz S., Hoi K. H., Mallik D., Sayah M., Organ M. G., Angew. Chem. Int. Ed., 2012, 51(14), 3314

    Article  CAS  Google Scholar 

  16. Liu G., Liu C., Zhao X., Wang J., RSC Adv., 2016, 6(50), 44475

    Article  CAS  Google Scholar 

  17. Liu G., Liu C., Han F., Wang Z., Wang J., Tetrahedron Lett., 2017, 58(8), 726

    Article  CAS  Google Scholar 

  18. Liu C., Liu G., Zhao H., Chin. J. Chem., 2016, 34(10), 1048

    Article  Google Scholar 

  19. Lan X. B., Chen F. M., Ma B. B., Shen D. S., Liu F. S., Organometallics, 2016, 35(22), 3852

    Article  CAS  Google Scholar 

  20. Ormerod D., Dorbec M., Merkul E., Kaval N., Lefèvre N., Hostyn S., Eykens L., Lievens J., Sergeyev S., Maes B. U. W., Org. Process Res. Dev., 2018, 22, 1509

    Article  CAS  Google Scholar 

  21. O’Brien C. J., Kantchev E. A. B., Valente C., Hadei N., Chass G. A., Lough A., Hopkinson A. C., Organ M. G., Chem. Eur. J., 2006, 12(18), 4743

    Article  Google Scholar 

  22. Rajabia F., Thiel W. R., Adv. Synth. Catal., 2014, 356, 1873

    Article  Google Scholar 

  23. Nasielski J., Hadei N., Achonduh G., Kantchev E. A. B., O’Brien C. J., Lough A., Organ M. G., Chem. Eur. J., 2010, 16(35), 10844

    Article  CAS  Google Scholar 

  24. Organ M. G., Calimsiz S., Sayah M., Hoi K. H., Lough A. J., Angew. Chem. Int. Ed., 2009, 48(13), 2383

    Article  CAS  Google Scholar 

  25. Valente C., Belowich M. E., Hadei N., Organ M. G., Eur. J. Org. Chem., 2010, 2010(23), 4343

    Google Scholar 

  26. Tu T., Sun Z., Fang W., Xu M., Zhou Y., Org. Lett., 2012, 14(16), 4250

    Article  CAS  Google Scholar 

  27. Lu D. D., He X. X., Liu F. S., J. Org. Chem., 2017, 82(20), 10898

    Article  CAS  Google Scholar 

  28. Ouyang J. S., Li Y. F., Huang F. D., Lu D. D., Liu F. S., ChemCat-Chem., 2018, 10(2), 371

    Article  CAS  Google Scholar 

  29. He X. X., Li Y., Ma B. B., Ke Z., Liu F. S., Organometallics., 2016, 35(16), 2655

    Article  CAS  Google Scholar 

  30. Dunsford J. J., Cavell K. J., Organometallics., 2014, 33(11), 2902

    Article  CAS  Google Scholar 

  31. Han F., Xu Y., Zhu R., Liu G., Chen C., Wang J., New J. Chem., 2018, 42(9), 7422

    Article  CAS  Google Scholar 

  32. Türkmen H., Çetinkaya B., J. Organomet Chem., 2006, 691(18), 3749

    Article  Google Scholar 

  33. Sheldrick G. M., SHELXL-97, Program for X-Ray Crystal Structure Solution, University of Göttingen, Göttingen, 1997

    Google Scholar 

  34. Dolomanov O. V., Bourhis L. J., Gildea R. J., Howard J. A. K., Puschmann H., J. Appl. Cryst., 2009, 42, 339

    Article  CAS  Google Scholar 

  35. Dash C., Shaikh M. M., Ghosh P., Eur. J. Inorg. Chem., 2009, 2009(12), 1608

    Article  Google Scholar 

  36. Organ M. G., Chass G. A., Fang D. C., Hopkinson A. C., Valente C., Synthesis, 2008, 17, 2776

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Yongfei Zeng or Guiyan Liu.

Additional information

Supported by the Natural Science Foundation of Tianjin City, China(No.16JCYBJC19700), the National Natural Science Foundation of China(No.21771138), and the Foundation of Development Program of Future Expert in Tianjin Normal University, China(No.WLQR201704).

Electronic supplementary material

40242_2019_9222_MOESM1_ESM.pdf

Highly Active Pd-PEPPSI Complexes for Suzuki-Miyaura Cross-coupling of Aryl Chlorides: an Investigation on the Effect of Electronic Properties

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, Y., Han, F., Zhang, M. et al. Highly Active Pd-PEPPSI Complexes for Suzuki-Miyaura Cross-coupling of Aryl Chlorides: an Investigation on the Effect of Electronic Properties. Chem. Res. Chin. Univ. 36, 859–864 (2020). https://doi.org/10.1007/s40242-019-9222-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-019-9222-2

Keywords

Navigation