SpringerLink
Log in

Direct use of nanoparticles as a heterogeneous catalyst: Pd0-doped CoFe2O4 magnetic nanoparticles for Sonogashira coupling reaction

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

Abstract

A magnetically separable nanocatalyst prepared by incorporating Pd nanoparticles onto CoFe2O4 magnetic nanoparticles was found to be very effective in catalyzing Sonogashira cross-coupling reactions. In this green synthetic process, it is not necessary to use an external linker to support the palladium nanoparticles onto the cobalt ferrite matrix. The catalyst is effective without the use of any ligand or copper additive. The reaction works smoothly in ethanol at 70 °C with both aryl iodides and bromides to produce corresponding product in high yield. After completion of the reaction, the catalyst could be easily separated using an external magnet and reused up to five catalytic cycles with sustained catalytic activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

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 includes VAT (France)

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 1
Fig. 6

Similar content being viewed by others

References

  1. M.B. Gawande, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 3371–3393 (2013)

    Article  CAS  Google Scholar 

  2. Y. Zhu, L.P. Stubbs, F. Ho, R. Liu, C.P. Ship, J.A. Maguire, N.S. Hosmane, ChemCatChem 2, 365–374 (2010)

    Article  CAS  Google Scholar 

  3. A.-H. Lu, E.L. Salabas, F. Schuth, Angew. Chem. Int. Ed. Engl. 46, 1222–1244 (2007)

    Article  CAS  Google Scholar 

  4. K.V.S. Ranganath, J. Kloesges, A.H. Schafer, F. Glorius, Angew. Chem. Int. Ed. Engl. 49, 7786–7789 (2010)

    Article  CAS  Google Scholar 

  5. N.T.S. Phan, H.V. Le, J. Mol. Catal. A 334, 130–138 (2011)

    Article  CAS  Google Scholar 

  6. K.K. Dey, K.K. Senapati, P. Phukan, S. Basu, A. Chattopadhyay, J. Phys. Chem. C 115, 12708–12715 (2011)

    Article  CAS  Google Scholar 

  7. K.K. Senapati, S. Roy, P. Phukan, J. Mol. Catal. A 352, 128–134 (2012)

    Article  CAS  Google Scholar 

  8. A. Serdar, K. Murat, V. Muervet, O. Saim, Appl. Catal. B 147, 387–393 (2014)

    Article  Google Scholar 

  9. M. Beygzadeh, A. Alizadeh, M.M. Khodaei, D. Kordestani, Catal. Commun. 32, 86–91 (2013)

    Article  CAS  Google Scholar 

  10. B.R. Vaddula, A. Saha, J. Leazer, R.S. Varma, Green Chem. 14, 2133–2136 (2012)

    Article  CAS  Google Scholar 

  11. K. Park, J.-M. You, S. Jeon, S. Lee, Eur. J. Org. Chem. 1973–1978 (2013)

  12. M.S. Maji, S. Murarka, A. Studer, Org. Lett. 12, 3878–3881 (2010)

    Article  CAS  Google Scholar 

  13. K. Sonogashira, J. Organomet. Chem. 653, 46–49 (2002)

    Article  CAS  Google Scholar 

  14. T. Mino, S. Suzuki, K. Hirai, M. Sakamoto, T. Fujita, Synlett, 3054–3131 (2011)

  15. R. Chinchilla, C. Najera, Chem. Soc. Rev. 40, 5084–5121 (2011)

    Article  CAS  Google Scholar 

  16. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 16, 4467–4470 (1975)

    Article  Google Scholar 

  17. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 108, 3054–3131 (2008)

    Article  CAS  Google Scholar 

  18. J.-H. Li, Y. Liang, Y.-X. **e, J. Org. Chem. 70, 4393–4396 (2005)

    Article  CAS  Google Scholar 

  19. E. Buxaderas, D.A. Alonso, C. Nájera, Eur. J. Org. Chem. 5864–5870 (2013)

  20. A. Soheili, J. Murry, J.A. Albaneze-Walker, P.G. Dormer, D.L. Hughes, Org. Lett. 5, 4191–4194 (2003)

    Article  CAS  Google Scholar 

  21. M. Larhed, A. Hallberg, J. Org. Chem. 61, 9582–9584 (1996)

    Article  CAS  Google Scholar 

  22. A. Arques, D. Aunon, P. Molina, Tetrahedron Lett. 45, 4337–4340 (2004)

    Article  CAS  Google Scholar 

  23. J. Cheng, Y. Sun, F. Wang, M. Guo, J.-H. Xu, Y. Pan, Z. Zhang, J. Org. Chem. 69, 5428–5432 (2004)

    Article  CAS  Google Scholar 

  24. B.H. Lipshutz, D.W. Chung, B. Rich, Org. Lett. 10, 3793–3796 (2008)

    Article  CAS  Google Scholar 

  25. L.-X. Shao, M. Shi, J. Org. Chem. 70, 8635–8637 (2005)

    Article  CAS  Google Scholar 

  26. A.O. King, N. Yasuda, Top. Organomet. Chem. 6, 205–245 (2004)

    CAS  Google Scholar 

  27. R. Chinchilla, C. Najera, Chem. Rev. 107, 874–922 (2007)

    Article  CAS  Google Scholar 

  28. J. Hassan, M. Sevignon, Ci. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 102, 1359–1470 (2002)

    Article  CAS  Google Scholar 

  29. E. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis (Wiley-Interscience, New York, 2002), pp. 229–409

    Book  Google Scholar 

  30. N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457–2483 (1995)

    Article  CAS  Google Scholar 

  31. N.T.S. Phan, M.V.D. Sluys, C.W. Jones, Adv. Synth. Catal. 348, 609–679 (2006)

    Article  CAS  Google Scholar 

  32. L. Xue, Z. Lin, Chem. Soc. Rev. 39, 1692–1705 (2010)

    Article  CAS  Google Scholar 

  33. A.M. Trzeciak, J.J. Ziolkowski, Coord. Chem. Rev. 249, 2308–2322 (2005)

    Article  CAS  Google Scholar 

  34. P. Das, U. Bora, A. Tairai, C. Sharma, Tetrahedron Lett. 51, 1479–1482 (2010)

    Article  CAS  Google Scholar 

  35. D. Mujahidin, S. Doye, Eur. J. Org. Chem. 2689–2693 (2005)

  36. A. Molnar, Chem. Rev. 111, 2251–2320 (2011)

    Article  CAS  Google Scholar 

  37. D. Astruc, Inorg. Chem. 46, 1884–1894 (2007)

    Article  CAS  Google Scholar 

  38. Z. Yinghuai, S.C. Peng, A. Emi, S. Zhenshum, R.K. Monalisa, Adv. Synth. Catal. 349, 1917–1922 (2007)

    Article  Google Scholar 

  39. L. Yin, J. Liebscher, Chem. Rev. 107, 133–173 (2007)

    Article  CAS  Google Scholar 

  40. M. Lamblin, L. Nassar-Hardy, J.-C. Hierso, E. Fouquet, F.Å.-X. Felpin, Adv. Synth. Catal. 352, 33–79 (2010)

    Article  CAS  Google Scholar 

  41. A. Modak, J. Mondal, A. Bhaumik, Green Chem. 14, 2840–2855 (2012)

    Article  CAS  Google Scholar 

  42. C. Cai, Y. He, J. Organomet. Chem. 696, 2689–2692 (2011)

    Article  Google Scholar 

  43. A.S. Roy, J. Mondal, B. Banerjee, P. Mondal, A. Bhaumik, S.M. Islam, Appl. Catal. A 469, 320–327 (2014)

    Article  CAS  Google Scholar 

  44. P. Veerakumar, M. Velayudham, K.-L. Lu, S. Rajagopal, Appl. Catal. A 455, 247–260 (2013)

    Article  CAS  Google Scholar 

  45. L.-M. Tan, Z.-Y. Sem, W.-Y. Chong, X. Liu, Hendra, W.L. Kwan, C.-L.K. Lee, Org. Lett. 15, 65–67 (2013)

    Article  CAS  Google Scholar 

  46. B.J. Borah, D.K. Dutta, J. Mol. Catal. A 366, 202–209 (2013)

    Article  CAS  Google Scholar 

  47. B.N. Lin, S.-H. Huang, W.-Y. Wu, C.-Y. Mou, F.-Y. Tsai, Molecules 15, 9157–9173 (2010)

    Article  CAS  Google Scholar 

  48. P. Dutta, A. Sarkar, Adv. Synth. Catal. 353, 2814–2822 (2011)

    Article  CAS  Google Scholar 

  49. S. El Hankari, A. El Kadib, A. Finiels, A. Bouhaouss, J.J.E. Moreau, C.M. Crudden, D. Brunel, P. Hesemann, Chem. Eur. J. 17, 8984–8994 (2011)

    Article  Google Scholar 

  50. M.-J. **, D.-H. Lee, Angew. Chem. Int. Ed. Engl. 49, 1119–1122 (2010)

    Article  CAS  Google Scholar 

  51. M. Choi, D.-H. Lee, K. Na, B.-W. Yu, R. Ryoo, Angew. Chem. Int. Ed. Engl. 48, 3673–3676 (2009)

    Article  CAS  Google Scholar 

  52. K. Komura, H. Nakamura, Y. Sugi, J. Mol. Catal. A 293, 72–78 (2008)

    Article  CAS  Google Scholar 

  53. C. Gonzalez-Arellano, A. Abad, A. Corma, H. Garcia, M. Iglesias, F. Sanchez, Angew. Chem. Int. Ed. Engl. 46, 1536–1538 (2007)

    Article  CAS  Google Scholar 

  54. M.B. Thathagar, G. Rothenberg, Org. Biomol. Chem. 4, 111–115 (2006)

    Article  CAS  Google Scholar 

  55. K.M. Dawood, W. Solodenko, A. Kirschning, ARKIVOC V, 104–124 (2007)

    Google Scholar 

  56. P. Rollet, W. Kleist, V. Dufaud, L. Djakovitch, J. Mol. Catal. A 241, 39–51 (2005)

    Article  CAS  Google Scholar 

  57. N. Kim, M.S. Kwon, C.M. Park, J. Park, Tetrahedron Lett. 45, 7057–7059 (2004)

    Article  CAS  Google Scholar 

  58. L. Djakovitch, P. Rollet, Tetrahedron Lett. 45, 1367–1370 (2004)

    Article  CAS  Google Scholar 

  59. K.K. Senapati, C. Borgohain, P. Phukan, J. Mol. Catal. A 339, 24 (2011)

    Article  CAS  Google Scholar 

  60. K.K. Senapati, C. Borgohain, K.C. Sarma, P. Phukan, J. Mol. Catal. A 346, 111–116 (2011)

    Article  CAS  Google Scholar 

  61. C. Borgohain, K.K. Senapati, K.C. Sarma, P. Phukan, J. Mol. Catal. A 363–364, 495–500 (2012)

    Article  Google Scholar 

  62. K.K. Senapati, C. Borgohain, P. Phukan, Catal. Sci. Technol. 2361–2366 (2012)

  63. C. Luo, Y. Zhang, Y. Wang, J. Mol. Catal. A 229, 7–12 (2005)

    Article  CAS  Google Scholar 

  64. C. Borgohain, K.K. Senapati, D. Mishra, K.C. Sarma, P. Phukan, Nanoscale 2, 2250–2256 (2010)

    Article  CAS  Google Scholar 

  65. X. Jia, D. Chen, X. Jiao, T. He, H. Wang, W. Jiang, J. Phys. Chem. C 112, 911–917 (2008)

    Article  CAS  Google Scholar 

  66. P. Vlazan, S.F. Rus, I. Grozescu, E. Vasile, Phys. Scr. T 157, 014047 (2013)

    Article  Google Scholar 

  67. M. Kaya, M. Zahmakiran, S. Özkar, M. Volkan, ACS Appl. Mater. Interfaces 4, 3866–3873 (2012)

    Article  CAS  Google Scholar 

  68. S. Akbayrak, M. Kaya, M. Volkan, S. Özkar, Appl. Catal. B 147, 387–393 (2004)

    Article  Google Scholar 

  69. B.D. Cullity, Elements of X-ray diffraction (Addison-Wesley, London, 1959), p. 261

    Google Scholar 

Download references

Acknowledgments

Financial support from DST, India (Grant No. SR/NM/NS-18/2011) is gratefully acknowledged. SR thanks UGC for a research fellowship. The authors would also like to acknowledge the support from SAIF-GU, SAIF-NEHU, and CIF of IIT Guwahati for analytical facilities during the course of investigations.

Author information

Authors and Affiliations

  1. Department of Chemistry, Gauhati University, Guwahati, 781014, India

    Subhasish Roy, Kula Kamal Senapati & Prodeep Phukan

Authors
  1. Subhasish Roy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kula Kamal Senapati
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Prodeep Phukan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Prodeep Phukan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 679 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Roy, S., Senapati, K.K. & Phukan, P. Direct use of nanoparticles as a heterogeneous catalyst: Pd0-doped CoFe2O4 magnetic nanoparticles for Sonogashira coupling reaction. Res Chem Intermed 41, 5753–5767 (2015). https://doi.org/10.1007/s11164-014-1699-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1699-1

Keywords

Search

Navigation