Skip to main content
SpringerLink
Log in

Mixed phosphine/N-heterocyclic carbene–palladium complexes: synthesis, characterization, crystal structure and application in the Sonogashira reaction in aqueous media

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

A series of 2-hydroxyethyl-substituted N-heterocyclic carbene–(NHC)PdX2PPh3 complexes have been synthesized by substitution of the pyridine or 3-chloropyridine ligand in (NHC)PdX2(pyridine/3-chloropyridine) complexes with triphenylphosphine. The new complexes were characterized by 1H, 13C {1H}, 31P {1H}NMR, FTIR spectroscopy and elemental analysis. Also, the molecular and crystal structures of 1c and 1d have been obtained by single-crystal X-ray diffraction. The 2-hydroxyethyl-substituted (NHC)PdX2PPh3 complexes have been examined as catalysts for the Sonogashira cross-coupling reaction in water/DMF solvent mixtures.

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

Similar content being viewed by others

References

  1. Lundgren RJ, Peters BD, Alsabeh PG, Stradiotto M (2010) Angew Chem Int Ed 49:4071

    Article  CAS  Google Scholar 

  2. Surry DS, Buchwald SL (2008) Angew Chem Int Ed 47:6338

    Article  CAS  Google Scholar 

  3. Guram AS, Buchwald SL (1994) J Am Chem Soc 116:7901

    Article  CAS  Google Scholar 

  4. Lin JCY, Huang RTW, Lee CS, Bhattacharyya A, Hwang WS, Lin IJB (2009) Chem Rev 109:3561

    Article  CAS  PubMed  Google Scholar 

  5. Ardueng AJ III, Harlow RL, Kline M (1991) J Am Chem Soc 113:361

    Article  Google Scholar 

  6. Dragutan V, Dragutan I, Delaude L, Demonceau A (2007) Coord Chem Rev 251:765

    Article  CAS  Google Scholar 

  7. Nirmala M, Viswanathamurthi P (2016) J Chem Sci 128:9

    Article  CAS  Google Scholar 

  8. Roymahapatra G, Samanta T, Seth SK, Mahapatra A, Chattopadhyay SK, Dinda J (2015) J Chem Sci 127:1057

    Article  CAS  Google Scholar 

  9. Velazquez HD, Verpoort F (2012) Chem Soc Rev 41:7032

    Article  CAS  PubMed  Google Scholar 

  10. Molnár Á (2011) Chem Rev 111:2251

    Article  CAS  PubMed  Google Scholar 

  11. Yin LX, Liebscher J (2007) Chem Rev 107:133

    Article  CAS  PubMed  Google Scholar 

  12. Sisodiya S, Wallenberg LR, Lewin E, Wendt OF (2015) Appl Catal A Gen 503:69

    Article  CAS  Google Scholar 

  13. Jin GY, Zhang XX, Cao S (2013) Org Lett 15:3114

    Article  CAS  PubMed  Google Scholar 

  14. CrysAlisPro Software System, Version 1.171.38.43 Rigaku Corporation (2015) Oxford UK

  15. Sheldrick GM (2015) Acta Crystallogr A 71:3

    Article  CAS  Google Scholar 

  16. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) J Appl Cryst 42:339

    Article  CAS  Google Scholar 

  17. Sheldrick GM (2015) Acta Crystallogr C 71:3

    Article  CAS  Google Scholar 

  18. Kumar A, Katari M, Ghosh P (2013) Polyhedron 52:524

    Article  CAS  Google Scholar 

  19. Aktaş A, Barut Celepci D, Gök Y, Aygün M (2018) ChemistrySelect 3:10932

    Article  CAS  Google Scholar 

  20. Aktaş A, Barut Celepci D, Gök Y, Aygün M (2018) ChemistrySelect 3:9974

    Article  CAS  Google Scholar 

  21. Dehimat ZI, Yaşar S, Tebbani D, Özdemir İ (2018) Inor Chim Acta 469:325

    Article  CAS  Google Scholar 

  22. Touj N, Yaşar S, Özdemir N, Hamdi N, Özdemir İ (2018) J Organomet Chem 860:59

    Article  CAS  Google Scholar 

  23. Boubakri L, Yaşar S, Dorcet V, Roisnel T, Bruneau C, Hamdi N, Özdemir İ (2017) New J Chem 41:5105

    Article  CAS  Google Scholar 

  24. Flanigan DM, Romanov-Michailidis F, White NA, Rovis T (2015) Chem Rev 115:9307

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Hahn FE, Lügger T, Beinhoff M (2004) Z Naturforsch 59b:196

    Article  Google Scholar 

  26. Huynh HV, Ho JHH, Neo TC, Koh LL (2005) J Organomet Chem 690:3854

    Article  CAS  Google Scholar 

  27. Calo´ V, Sole RD, Nacci A, Schingaro E, Scordari F (2000) Eur J Org Chem 2000:869

    Article  Google Scholar 

  28. Kernbach U, Lügger T, Hahn FE, Fehlhammer WP (1997) J Organomet Chem 541:51

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors acknowledge Dokuz Eylül University for the use of the Oxford Rigaku Xcalibur Eos Diffractometer (purchased under University Research Grant No: 2010.KB.FEN.13). The authors thank the İnönü University Faculty of Science Department of Chemistry for the spectroscopy data and İnönü University Scientific and Technology Center for the elemental analyses of the compounds.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, İnönü University, 44280, Malatya, Turkey

    Aydın Aktaş, Fatoş Erdemir & Yetkin Gök

  2. Department of Physics, Faculty of Science, Dokuz Eylül University, 35160, Buca, İzmir, Turkey

    Duygu Barut Celepci & Muhittin Aygün

Authors
  1. Aydın Aktaş
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fatoş Erdemir
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Duygu Barut Celepci
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yetkin Gök
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Muhittin Aygün
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aydın Aktaş.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 626 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Aktaş, A., Erdemir, F., Barut Celepci, D. et al. Mixed phosphine/N-heterocyclic carbene–palladium complexes: synthesis, characterization, crystal structure and application in the Sonogashira reaction in aqueous media. Transit Met Chem 44, 229–236 (2019). https://doi.org/10.1007/s11243-018-0286-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-018-0286-5

Search

Navigation