Skip to main content
SpringerLink
Log in

Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

In the current study, five novel perimidinium chlorides were synthesized in good yields by reaction of 1-(3-methylbenzyl)perimidine with five different alkyl chlorides under microwave irradiation in 30 minutes. Synthesized compounds were characterized by IR, 1H, 13C NMR spectroscopic methods and elemental analyses. Performance of in situ formed catalytic system which consist of the perimidinium salts and Pd(OAc)2 was investigated for Heck and Suzuki reactions in aqueous media, and desired products were obtained in good yields.

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

Similar content being viewed by others

References

  1. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.

    Article  CAS  Google Scholar 

  2. Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.

    Article  CAS  Google Scholar 

  3. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.

    Article  Google Scholar 

  4. Beletskaya, I. P.; Cheprakov, A. Chem. Rev. 2000, 100, 3009.

    Article  CAS  Google Scholar 

  5. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.

    Article  CAS  Google Scholar 

  6. Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.

    Article  CAS  Google Scholar 

  7. Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151.

    Article  CAS  Google Scholar 

  8. Kovala-Demertzi, D.; Kourkoumelis, N.; Derlat, K.; Michalak, J.; Andreadaki, F. J.; Kostas, I. D. Inorg. Chim. Acta 2008, 361, 1562.

    Article  CAS  Google Scholar 

  9. An der Heiden, M.; Plenio, H. Chem.–Eur. J. 2004, 10, 1789.

  10. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.

    Article  CAS  Google Scholar 

  11. Zhou, Z.; Liu, M.; Wu, X.; Yu, H.; Xu, G.; Xie, Y. Appl. Organomet. Chem. 2013, 27, 562.

    CAS  Google Scholar 

  12. Sierra, D.; Bhuvanesh, N.; Reibenspies, J. H.; Gladysz, J. A.; Klahn, A. H. J. Organomet. Chem. 2014, 749, 416.

    Article  CAS  Google Scholar 

  13. Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. 1995, 34, 2371.

    Article  CAS  Google Scholar 

  14. Tang, Y.-Q.; Lu, J.-M.; Shao, L.-X. J. Organomet. Chem. 2011, 696, 3741.

    Article  CAS  Google Scholar 

  15. Pavia, C.; Ballerini, E.; Bivona, L. A.; Giacalone, F.; Aprile, C.; Vaccaro, L.; Gruttadauria, M. Adv. Synth. Catal. 2013, 355, 2007.

    Article  CAS  Google Scholar 

  16. Ozdemir, I.; Yigit, M.; Cetinkaya, E.; Cetinkaya, B. Appl. Organomet. Chem. 2006, 20, 187.

    Article  CAS  Google Scholar 

  17. Demir, S.; Zengin, R.; Ozdemir, I. Heteroat. Chem. 2013, 24, 77.

    Article  CAS  Google Scholar 

  18. Demir, S.; Ozdemir, I.; Cetinkaya, B. Appl. Organomet. Chem. 2006, 20, 254.

    Article  CAS  Google Scholar 

  19. Gulcemal, S.; Kahraman, S.; Daran, J. C.; Cetinkaya, E.; Cetinkaya, B. J. Organomet. Chem. 2009, 694, 3580.

    Article  CAS  Google Scholar 

  20. Bazinet, P.; Yap, G. P. A.; Richeson D. S. J. Am. Chem. Soc. 2003, 125, 13314.

    Article  CAS  Google Scholar 

  21. Alici, B.; Ozdemir, I.; Karaaslan, K.; Çetinkaya, E.; Cetinkaya, B. J. Mol. Catal. A: Chem. 2005, 231, 261.

    Article  CAS  Google Scholar 

  22. Ozdemir, I.; Alici, B.; Gurbuz, N.; Cetinkaya, B.; Çetinkaya E. Russ. J. Coord. Chem. 2005, 31, 142.

    Article  Google Scholar 

  23. Tu, T.; Malineni, J.; Bao, X.; Dötz, K. H. Adv. Synth. Catal. 2009, 351, 1029.

    Article  CAS  Google Scholar 

  24. Tsurugi, H.; Fujita, S.; Choi, G.; Yamagata, T.; Ito, S.; Miyasaka, H.; Mashima, K. Organometallics 2010, 29, 4120.

    Article  CAS  Google Scholar 

  25. Chou, C.-C.; Yang, C.-C.; Syu, H.-B.; Kuo, T.-S. J. Organomet. Chem. 2013, 745-746, 387.

    Article  CAS  Google Scholar 

  26. Arzu Akinci, P.; Gulcemal, S.; Kazheva, O. N.; Alexandrov, G. G.; Dyachenko, O. A.; Cetinkaya, E.; Cetinkaya B. J. Organomet. Chem. 2014, 765, 23.

    Article  Google Scholar 

  27. Bassyouni, F. A.; Abu-Bakr, S. M.; Hegab, K. H.; El-Eraky, W.; El Beih, A. A.; Abdel Rehim, M. E. Res. Chem. Intermed. 2012, 38, 1527.

    Article  CAS  Google Scholar 

  28. Azam, M.; Warad, I.; Al-Resayes, S.; Zahin, M.; Ahmad, I.; Shakir, M. Z. Anorg. Allg. Chem. 2012, 638, 881.

    Article  CAS  Google Scholar 

  29. Azam, M.; Warad, I.; Al-Resayes, S. I.; Alzaqri, N.; Khan, M. R.; Pallepogu, R.; Dwivedi, S.; Musarrat, J.; Shakir, M. J. Mol. Struct. 2013, 1047, 48.

    Article  CAS  Google Scholar 

  30. Chan, A. H.; Wereszczynski, J.; Amer, B. R.; Yi, S. W.; Jung, M. E.; McCammon, J. A.; Clubb, R. T. Chem. Biol. Drug Des. 2013, 82, 418.

    Article  CAS  Google Scholar 

  31. Farghaly, T. A.; Mahmoud, H. K. Arch. Pharm. (Weinheim, Ger.) 2013, 346, 392.

    Article  CAS  Google Scholar 

  32. Koca, I.; Ungoren, S. H.; Kibriz, I. E.; Yilmaz, F. Dyes Pigm. 2012, 95, 421.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Inonu University, Road of Elazig, 15th km., Post Office Box No: 44280, Malatya, Turkey

    Gulnihan Onar, Mert Olgun Karatas & Bülent Alici

  2. Department of Chemistry, Faculty of Sciences, Ege University, Neighborhood of Erzene, Bornova Post Office Box No: 35040, Izmir, Turkey

    Engin Cetinkaya

Authors
  1. Gulnihan Onar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mert Olgun Karatas
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bülent Alici
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Engin Cetinkaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mert Olgun Karatas.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 563–567

Electronic supplementary material

Supplementary information to this article containing 1H and 13C NMR spectra of compounds 1, 2a–e is available for authorized users.

ESM 1

(PDF 644 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Onar, G., Karatas, M.O., Alici, B. et al. Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions. Chem Heterocycl Comp 51, 563–567 (2015). https://doi.org/10.1007/s10593-015-1732-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1732-3

Keyword

Search

Navigation