Skip to main content
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


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

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

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

Similar content being viewed by others


  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).!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 (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


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


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).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: