Skip to main content
SpringerLink
Log in

Palladium complexes bearing the dipyridyl ligand: synthesis, structural studies, and use in the Heck reaction

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Two new palladium complexes derived from the di(2-pyridinyl)methanone N-(2-pyridinyl)hydrazone (DPMNPH) ligand are reported. The compounds were characterized by elemental analysis, spectroscopic studies, and, for the DPMNPH ligand, single-crystal X-ray diffraction analysis. The DPMNPH ligand crystallized as orthorhombic with the space group P212121. The H1 atom is intramolecularly bonded to the pyridinic N4 with N1–H1 = 0.92(3) Å, H1···N4 = 1.87(2) Å, N1···N4 = 2.615(2) Å, and N1–H1···N4 = 137(2)°. Both complexes were excellent catalysts in the Heck reaction in the presence of base.

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
Scheme 2
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. M.C. Feller, R. Robson, Aust. J. Chem. 21, 2919 (1968)

    Article  CAS  Google Scholar 

  2. A.C. Casado, G. Barandika, B. Bazan, M.-K. Urtiagaa, M.-I. Arriortuaa, CrystEngComm 15, 5134–5143 (2013)

    Article  Google Scholar 

  3. C. Godard, S.B. Dyckett, S. Parsons, R.N. Perutz, Chem. Commun. 18, 23332 (2004)

    Google Scholar 

  4. C. Mock, I. Puscasu, M.J. Rauterkus, G. Tallen, J.E.A. Wolf, B. Krebs, Inorg. Chim. Acta 319, 109 (2001)

    Article  CAS  Google Scholar 

  5. A. C. Deveson, S. L. Hearth, C. J. Harding, A. K. Powell, J. Chem. Soc. Dalton Trans. 3173 (1996). http://pubs.rsc.org/en/content/articlelanding/1996/dt/dt9960003173#!divAbstract

  6. S. Kar, N. Chanda, S.M. Mobin, F.A. Urbanos, M. Niemeyer, V.G. Puranik, R. Jimenez-Aparico, G.K. Lahiri, Inorg. Chem. 44, 1571 (2005)

    Article  CAS  Google Scholar 

  7. J.F. Berry, F.A. Cotton, L.M. Daniels, C.A. Murillo, X. Wang, Inorg. Chem. 42, 2418 (2003)

    Article  CAS  Google Scholar 

  8. Y. Zhang, X.-Z. Sun, Y.-H. Deng, S.-L. Cao, C.-Q. Wan, Inorg. Chim. Acta 421, 411–415 (2014)

    Article  CAS  Google Scholar 

  9. J. Tsuji, Palladium Reagents and Catalysts. Chapter 3 (Wiley, New York, 2004)

    Book  Google Scholar 

  10. F. Diederich, P.J. Stang, Metal-Catalyzed Cross-Coupling Reactions (VCH, Weinheim, 1997)

    Google Scholar 

  11. N. Shahnaz, B. Banik, P. Das, Tetrahedron Lett. 54, 2886 (2013)

    Article  CAS  Google Scholar 

  12. M. Keles, H. Keles, D.M. Emir, Appl. Organometal. Chem. 29, 543–548 (2015)

    Article  CAS  Google Scholar 

  13. M.N. Alam, S.M. Sarkar, M.R. Miah, Catal. Lett 98, 383–389 (2009)

    Article  CAS  Google Scholar 

  14. M. Bakherad, A. Keivanloo, S. Samangooei, Tetrahedron Lett. 53(2012), 5773–5776 (2012)

    Article  CAS  Google Scholar 

  15. I. Warad, M. Azam, S.I. Al-Resayes, M.S. Khan, P. Ahmad, M. Al-Nuri, S. Jodeh, A. Husein, S.F. Haddad, B. Hammouti, M. Al-Noaimi, Inorg. Chem. Commun. 43, 155–161 (2014)

    Article  CAS  Google Scholar 

  16. M. Bagherzadeh, M. Amini, A. Ellern, L.K. Woo, Inorg. Chim. Acta 383, 46 (2012)

    Article  CAS  Google Scholar 

  17. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171.NET) (compiled May 16 2011)

  18. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. 42, 339 (2009)

    Article  CAS  Google Scholar 

  19. G.M. Sheldrick, SHELXTL version 6.10, Structure Determination Software Suite (Bruker AXS Inc., Madison, 2000)

    Google Scholar 

  20. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds (Wiley, New York, 1986)

    Google Scholar 

  21. L.J. Baucher, J. Inorg. Nucl. Chem. 36, 531 (1974)

    Article  Google Scholar 

  22. G.R. Garcia, N.A. Lopez, J.G.A. Rodriguez, D.M. Otero, R.F. Esparzo, M.F. Alamo, Polyhedron Polyhedron 30, 1324 (2011)

    Article  Google Scholar 

  23. V.L. Siji, M.R. Sudarsanakumar, S. Suma, Polyhedron 29, 2035 (2010)

    Article  CAS  Google Scholar 

  24. A.B.P. Lever, Inorganic Electronic Spectroscopy, 2nd edn. (Elsevier, New York, 1984)

    Google Scholar 

  25. M. Ulusoy, O. Birel, O. Sahin, O. Buyukgungor, B. Cetinkya, Polyhedron 38, 141 (2012)

    Article  CAS  Google Scholar 

  26. F. Alono, I.P. Beletskaya, M. Yus, Tetrahedron 61, 11771 (2005)

    Article  Google Scholar 

  27. G.P. Chiusoli, M. Catellani, M. Costa, E. Motti, N.D. Ca, G. Maestri, Coord. Chem. Rev. 254, 456 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to extend their sincere appreciation to the Dean of Scientific Research at King Saud University for funding this work through research group number RG -1435-091.

Author information

Authors and Affiliations

  1. Department of Chemistry, Science College, AN-Najah National University, P.O. Box 7, Nablus, State of Palestine

    Ismail Warad

  2. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451, KSA

    Mohammad Azam, Saud I. Al-Resayes & Mohammad Shahidul Islam

  3. Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, KSA

    Sarfaraz Ahmed

  4. Department of Chemistry, Hashemite University, Zarqa, 13115, Jordan

    Salim F. Haddad

Authors
  1. Ismail Warad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Azam
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Saud I. Al-Resayes
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mohammad Shahidul Islam
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sarfaraz Ahmed
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Salim F. Haddad
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Azam.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 304 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Warad, I., Azam, M., Al-Resayes, S.I. et al. Palladium complexes bearing the dipyridyl ligand: synthesis, structural studies, and use in the Heck reaction. Res Chem Intermed 42, 379–389 (2016). https://doi.org/10.1007/s11164-015-2256-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2256-2

Keywords

Search

Navigation