Skip to main content
SpringerLink
Log in

Microwave Assisted Ligand Free Palladium Catalyzed Synthesis of β-Arylalkenyl Nitriles Using Water as Solvent

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

We have developed a rapid and efficient method for the synthesis of β-arylalkenyl nitriles by one pot three component coupling reaction of diphenyl acetylene, K4(Fe)CN6, and aryl halides using Pd(OAc)2 as a catalyst and water as a solvent under microwave irradiation. The method is very simple and attractive as it requires only a shorted reaction time and employs cyanide source which is safe and inexpensive.

Graphical Abstract

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. Chinchilla R, Najera C (2007) Chem Rev 107:874

    Article  CAS  Google Scholar 

  2. Reetz MT, De Vries JG (2004) Chem Commun 1559

  3. Gwilherm E, Blanchard N, Toumi M (2008) Chem Rev 108:3054

    Article  Google Scholar 

  4. Brandsma L, Vasilevsky SF, Verkruijsse HD (1998) Application of transition metal catalysts in organic synthesis. Springer, Berlin

    Google Scholar 

  5. Kleemann A, Engel J, Kutscher B, Reichert D (2001) Pharmaceutical substances: syntheses, patents, applications, 4th edn. Georg Thieme, Stuttgart

    Google Scholar 

  6. Collier SJ, Langer P (2004) Sci Synth 19:403

    Google Scholar 

  7. Rosenmund KW, Struck E (1919) Ber Dtsch Chem Ges 2:1749

    Google Scholar 

  8. Lindley J (1984) Tetrahedron 40:1433

    Article  CAS  Google Scholar 

  9. Sundermeier M, Zapf A, Mutyala S, Baumann W, Sans J, Weiss S, Beller M (2003) Chem Eur J 9:1828 For a review

    Article  CAS  Google Scholar 

  10. Schareina T, Zapf A, Beller M (2004) Chem Commun 1388

  11. Cheng YN, Duan Z, Yu LJ, Li ZX, Zhu Y, Wu YJ (2008) Org Lett 10:901

    Article  CAS  Google Scholar 

  12. Schareina T, Zapf A, Beller M (2005) Tetrahedron Lett 46:2585

    Article  CAS  Google Scholar 

  13. Weissman SA, Zewge D, Chen C (2005) J Org Chem 70:1502

    Article  Google Scholar 

  14. Zhu YZ, Cai C (2007) Eur J Org Chem 15:2401

    Article  Google Scholar 

  15. Zhu YZ, Cai C (2007) Synth Commun 37:3359

    CAS  Google Scholar 

  16. Velmathi S, Leadbeater NE (2008) Tetrahedron Lett 49:4693

    Article  CAS  Google Scholar 

  17. Toginelli A, Gevariya H, Alongi M, Botta M (2007) Tetrahedron Lett 48:4801

    Article  Google Scholar 

  18. Bagley MC, Dix MC, Fusillo V (2009) Tetrahedron Lett 50:3661

    Article  CAS  Google Scholar 

  19. Prasad A, Eycken EV (2008) Eur J Org Chem 1133 (For micro review)

  20. Kappe CO (2004) Angew Chem Int Ed 43:6250 For microwave chemistry Reviews

    Article  CAS  Google Scholar 

  21. Majetich G, Whiteless K (1997) In: Kingston HM, Haswell SJ (eds.) Microwave-enhanced chemistry: fundamentals, sample preparation, and applications. ACS, Washington, DC

  22. Hayes BL (2002) Microwave synthesis: chemistry at the speed of light. CEM, Matthews

    Google Scholar 

  23. Cao H, Xiao WJ (2005) Can J Chem 83:826

    Article  CAS  Google Scholar 

  24. Yang Q, Li XY, Wu H, Xiao WJ (2006) Tetrahedron Lett 47:3893

    Article  CAS  Google Scholar 

  25. Larhed M, Moberg C, Hallberg A (1996) Tetrahedron Lett 37:8219

    Article  CAS  Google Scholar 

  26. Narendar N, Velmathi S (2009) Tetrahedron Lett 50:5159

    Article  CAS  Google Scholar 

  27. Nakao Y, Oda S, Hiyama T (2004) J Am Chem Soc 126:13904

    Article  CAS  Google Scholar 

Download references

Acknowledgments

One of the authors S.V gratefully acknowledges the support and funding from Dr. M. Chidambaram, the Director of NITT and DST (SR/FTP/CS-142-2006). This work was also partially supported by the Ministry of Education, Culture, Sports, Science and Technology (MEXT) under the Strategic Program for Building an Asian Science and Technology Community Scheme and World Premier International Research Center (WPI) Initiative on Materials Nanoarchitectonics, MEXT, Japan.

Author information

Authors and Affiliations

  1. Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology, Tiruchirappalli, Tamil Nadu, 620 015, India

    Sivan Velmathi & Reena Vijayaraghavan

  2. International Center for Materials Nanoarchitectonics, World Premier International (WPI) Research Initiative, National Institute for Materials Science, Tsukuba, Ibaraki, 305-0044, Japan

    Sivan Velmathi, Ravindra P. Pal & Ajayan Vinu

Authors
  1. Sivan Velmathi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Reena Vijayaraghavan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ravindra P. Pal
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ajayan Vinu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sivan Velmathi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Velmathi, S., Vijayaraghavan, R., Pal, R.P. et al. Microwave Assisted Ligand Free Palladium Catalyzed Synthesis of β-Arylalkenyl Nitriles Using Water as Solvent. Catal Lett 135, 148–151 (2010). https://doi.org/10.1007/s10562-010-0279-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-010-0279-2

Keywords

Search

Navigation