Skip to main content
SpringerLink
Log in

N-Propylphthalimide-substituted bis-(NHC)PdX2 complexes: synthesis, characterization and catalytic activity in direct arylation reactions

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

Palladium-catalyzed direct arylation of heteroaromatics has become a popular method for producing carbon–carbon bonds via C–H bond activation. A wide diversity of heteroaromatics such as furan, thiophenes and thiazoles can be used for this reaction. This paper reports the synthesis of N-propylphthalimide-substituted bis-(NHC)PdX2 complexes (NHC = N-heterocyclic carbene), and their catalytic activity in direct arylation reactions. The complexes have been prepared from Ag(I)NHC precursors by transmetallation and characterized by spectroscopy and elemental analysis. The bis-(NHC)PdX2 complexes show excellent activity as catalysts in the direct arylation reactions of 2-n-butylfuran, 2-n-butylthiophene and 2-isopropylthiazole.

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
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Kakiuchi F, Murai S (2002) Acc Chem Res 35:826

    Article  CAS  Google Scholar 

  2. Miura M, Nomura M (2002) Top Curr Chem 219:211

    Article  CAS  Google Scholar 

  3. Kakiuchi F, Chatani N (2003) Adv Synth Catal 345:1077

    Article  CAS  Google Scholar 

  4. Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174

    Article  CAS  Google Scholar 

  5. Sun L, Li H, Yu D-G, Yu M, Zhou X, Lu X-Y, Huang K, Zheng S-F, Li B-J, Shi Z-J (2010) Nat Chem 2:1044

    Article  CAS  Google Scholar 

  6. Liu W, Cao H, Lei A (2010) Angew Chem Int Ed 49:2004

    Article  CAS  Google Scholar 

  7. Stanforth SP (1998) Tetrahedron 54:263

    Article  CAS  Google Scholar 

  8. Hassan M, Se’vignon M, Gozzi C, Shulz E, Lemaire M (2002) Chem Rev 102:1359

    Article  CAS  Google Scholar 

  9. Miura M, Nomura M (2002) Top Curr Chem 219:211

    Article  CAS  Google Scholar 

  10. Kakiuchi F, Chatani N (2003) Adv Synth Catal 345:1077

    Article  CAS  Google Scholar 

  11. Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174

    Article  CAS  Google Scholar 

  12. Yokooji A, Satoh T, Miura M, Nomura M (2004) Tetrahedron 60:6757

    Article  CAS  Google Scholar 

  13. Campeau L-C, Rousseaux S, Fagnou K (2005) J Am Chem Soc 127:18020

    Article  CAS  Google Scholar 

  14. Do H-Q, Khan RMK, Daugulis O (2008) J Am Chem Soc 130:15185

    Article  CAS  Google Scholar 

  15. Liégault B, Lapointe D, Caron L, Vlassova A, Fagnou KJ (2009) Org Chem 74:1826

    Article  Google Scholar 

  16. Ueda K, Yanagisawa S, Yamaguchi J, Itami K (2010) Angew Chem Int Ed 49:8946

    Article  CAS  Google Scholar 

  17. Tamba S, Fuji R, Mori A, Hara K, Koumura N (2011) Chem Lett 40:922

    Article  CAS  Google Scholar 

  18. Fu HY, Chen L, Doucet H (2012) J Org Chem 77:4473

    Article  CAS  Google Scholar 

  19. Reddy VP, Qiu R, Iwasaki T, Kambe N (2013) Org Lett 15:1290

    Article  CAS  Google Scholar 

  20. Bheeter CB, Chen L, Soulé J-F, Doucet H (2016) Catal Sci Technol 6:2005

    Article  CAS  Google Scholar 

  21. Yuan K, Doucet H (2013) Chem Cat Chem 5:3495

    CAS  Google Scholar 

  22. Tsurugi H, Yamamoto K, Nagae H, Kaneko H, Mashima K (2014) Dalton Trans 43:2331

    Article  CAS  Google Scholar 

  23. Khake SM, Jagtap RA, Dangat YB, Gonnade RG, Vanka K, Punji B (2016) Organometallics 35:875

    Article  CAS  Google Scholar 

  24. Abdellaoui F, Youssef C, Ammar HB, Roisnel T, Soulé J-F, Doucet H (2016) ACS Catal 6:4248

    Article  CAS  Google Scholar 

  25. Akkoç S, Gök Y (2015) Inorg Chim Acta 429:34

    Article  Google Scholar 

  26. Yiğit M, Yiğit B, Gök Y (2016) Inorg Chim Acta 453:23

    Article  Google Scholar 

  27. Lin N-C, Syu HJH, Naziruddin AR, Liu F-C, Lin IJB (2017) RSC Adv 7:11652

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. Peris E, Crabtree RH (2004) Coord Chem Rev 248:2239

    Article  CAS  Google Scholar 

  30. Burling S, Whittlesey MK, Williams JMJ (2005) Adv Synth Catal 347:591

    Article  CAS  Google Scholar 

  31. Zhang CM, Trudell ML (2000) Tetrahedron Lett 41:595

    Article  CAS  Google Scholar 

  32. Akkoç S, Gök Y (2014) Appl Organometal Chem 28:854

    Article  Google Scholar 

  33. Sarı Y, Aktaş A, Barut Celepci D, Gök Y, Aygün M (2017) Catal Lett 147:2340

    Article  Google Scholar 

  34. Gök Y, Akkoç S, Erdoğan H, Albayrak S (2016) J Enzym Inhib Med Chem 31:1322

    Article  Google Scholar 

  35. Yiğit M, Yiğit B, Gök Y (2016) Inorg Chim Acta 453:23

    Article  Google Scholar 

Download references

Acknowledgements

This work was financially supported by İnönü University Research Fund (IUBAP 2012/02) and the authors acknowledge 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

    Hülya Erdoğan, Aydın Aktaş, Yetkin Gök & Yakup Sarı

Authors
  1. Hülya Erdoğan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Aydın Aktaş
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yetkin Gök
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yakup Sarı
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aydın Aktaş.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Erdoğan, H., Aktaş, A., Gök, Y. et al. N-Propylphthalimide-substituted bis-(NHC)PdX2 complexes: synthesis, characterization and catalytic activity in direct arylation reactions. Transit Met Chem 43, 31–37 (2018). https://doi.org/10.1007/s11243-017-0190-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-017-0190-4

Search

Navigation