Skip to main content
SpringerLink
Log in

Synthesis, crystal structures, and catalytic activities of palladium imidazole complexes formed by 2-hydroxyethyl group cleavage

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

N-4,6-dimethyl-2-pyrimidinylimidazole 1 and its hydroxyethyl derivative 1-(2-hydroxyethyl)-3-(4,6-dimethyl-2-pyrimidinyl)imidazolium chloride 2 have been synthesized and characterized. The attempted synthesis of bis(N-heterocyclic carbene)palladium complexes via the direct reaction of 2 with Pd(OAc)2 results in the unexpected formation of a bis(N-arylimidazole) palladium complex 3. Additionally, the analogous bis(N-methylimidazole) palladium complex 4 has also been synthesized by the above method. Compounds 1–4 were characterized by elemental analysis, IR, and 1H NMR. Additionally, their crystal structures have been determined by X-ray diffraction. Complexes 3 and 4 were found to be efficient catalysts for the Suzuki reaction.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    Article  CAS  Google Scholar 

  2. Suzuki A (2002) J Organomet Chem 653:83

    Article  CAS  Google Scholar 

  3. Phan NTS, Sluys MVD, Jones CW (2006) Adv Synth Catal 348:609

    Article  CAS  Google Scholar 

  4. Herrmann WA (2002) Angew Chem Int Ed 41:1290

    Article  CAS  Google Scholar 

  5. Ender D, Niemeier O, Henseler A (2007) Chem Rev 107:5606

    Article  Google Scholar 

  6. Nolan SP (ed) (2006) N-Heterocyclic carbenes in synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  7. Kantchev EAB, O’Brien CJ, Organ MG (2007) Angew Chem Int Ed 46:2768

    Article  CAS  Google Scholar 

  8. Fortman GC, Nolan SP (2011) Chem Soc Rev 40:5151

    Article  CAS  Google Scholar 

  9. Benhamou L, Chardon E, Lavigne G, Bellemin-Laponnaz S, César V (2011) Chem Rev 111:2705

    Article  CAS  Google Scholar 

  10. Crudden CM, Allen DP (2004) Coord Chem Rev 248:2247

    Article  CAS  Google Scholar 

  11. Schuster O, Yang LR, Raubenheimer HG, Albrecht M (2009) Chem Rev 109:3445

    Article  CAS  Google Scholar 

  12. Xu C, Zhang YP, Wang ZQ, Fu WJ, Hao XQ, Xu Y, Ji BM (2010) Chem Commun 6852

  13. Xu C, Wang ZQ, Zhang YP, Dong XM, Hao XQ, Fu WJ, Ji BM, Song MP (2011) Eur J Inorg Chem 4878

  14. Xu C, Lu YX, Lou XH, Wang ZQ, Fu WJ, Ji BM (2011) Transition Met Chem 36:637

    Article  CAS  Google Scholar 

  15. Xu C, Hao XQ, Li Z, Dong XM, Duan LM, Wang ZQ, Ji BM, Song MP (2012) Inorg Chem Commun. doi:10.1016/j.inoche.2011.12.009

    Google Scholar 

  16. Branco LC, Rosa JN, Ramos JJM, Afonso CAM (2002) Chem Eur J 8:3671

    Article  CAS  Google Scholar 

  17. Xu C, Wang ZQ, Fu WJ, Lou XH, Li YF, Cen FF, Ma HJ, Ji BM (2009) Organometallics 28:1909

    Article  CAS  Google Scholar 

  18. Szulmanowicz MS, Zawartka W, Gniewek A, Trzeciak AM (2010) Inorg Chim Acta 363:4346

    Article  CAS  Google Scholar 

  19. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  Google Scholar 

  20. Batey RA, Shen M, Lough AJ (2002) Org Lett 4:1411

    Article  CAS  Google Scholar 

  21. Caddick S, Cloke FGN, Hitchcock PB, Lewis AKK (2004) Angew Chem Int Ed 43:5824

    Article  CAS  Google Scholar 

  22. Wang ZG, Sun HM, Yao HS, Shen Q, Zhang Y (2006) Organometallics 25:4436

    Article  CAS  Google Scholar 

  23. Liu LJ, Wang F, Shi M (2009) Eur J Inorg Chem 1723

  24. Sabiah S, Lee CS, Hwang WS, Lin IJB (2010) Organometallics 29:290

    Article  CAS  Google Scholar 

  25. Kurdziel K, Olejniczak S, Okruszek A, Glowiak T, Kruszyński Materazzi S, Potrzebowski MJ (2006) J Organomet Chem 619:869

    Article  Google Scholar 

  26. Xi CJ, Wu YW, Yan XY (2008) J Organomet Chem 693:3842

    Article  CAS  Google Scholar 

  27. Mathews CJ, Smith PJ, Welton T (2003) J Mol Catal A: Chem 206:77

    Article  CAS  Google Scholar 

  28. Mathews CJ, Smith PJ, Welton T (2004) J Mol Catal A: Chem 214:27

    Article  CAS  Google Scholar 

  29. Kawamura K, Haneda S, Gan Z, Eda K, Hayashi M (2008) Organometallics 27:3748

    Article  CAS  Google Scholar 

  30. Kudo N, Perseghini M, Fu GC (2006) Angew Chem Int Ed 45:1282

    Article  CAS  Google Scholar 

  31. Billingsley KL, Anderson KW, Buchwald SL (2006) Angew Chem Int Ed 45:3484

    Article  CAS  Google Scholar 

  32. Billingsley KL, Buchwald SL (2007) J Am Chem Soc 129:3358

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 20902043) and the Natural Science Foundation of Henan Province and Henan Education Department, China (Nos. 102300410220 and 2009B150019) for financial support of this work.

Author information

Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, 471022, Henan, China

    Chen Xu, Zhi-Qiang Wang & Wei-Jun Fu

  2. Department of Chemistry, Zhengzhou University, Zhengzhou, 450052, Henan, China

    Zhen Li, Lu-Meng Duan, Xin-Qi Hao & Mao-Ping Song

Authors
  1. Chen Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhen Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lu-Meng Duan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhi-Qiang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wei-Jun Fu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xin-Qi Hao
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Mao-Ping Song
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chen Xu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xu, C., Li, Z., Duan, LM. et al. Synthesis, crystal structures, and catalytic activities of palladium imidazole complexes formed by 2-hydroxyethyl group cleavage. Transition Met Chem 37, 373–378 (2012). https://doi.org/10.1007/s11243-012-9598-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-012-9598-z

Keywords

Search

Navigation