Skip to main content
Log in

Triton X-100 stabilized Pd nanoparticles and their catalytic application in one-pot sequential Heck and Hiyama coupling in water

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

Abstract

In situ-generated palladium nanoparticles (Pd NPs) using Triton X-100 non-ionic surfactant-catalyzed one-pot sequential Hiyama and Heck coupling reactions in water under aerobic conditions has been demonstrated. The reaction was highly efficient for the synthesis of symmetrical stillbenes utilizing arenediazonium salts and vinyl triethoxy silane. The in situ-generated Pd NPs were characterized by transmission electron microscopy analysis and had a size below 20 nm. The aqueous system containing the surfactant along with the Pd NPs was recycled five times, without significant loss of catalytic activity.

Graphical Abstract

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

Access this article

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

Instant access to the full article PDF.

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

Similar content being viewed by others

References

  1. M.A. Dube, S. Salehpour, Macromol. React. Eng. 8, 7–28 (2014)

    Article  CAS  Google Scholar 

  2. C.-J. Li, Chem. Rev. 105, 3095–3166 (2005)

    Article  CAS  Google Scholar 

  3. P.E. Savage, Chem. Rev. 99, 603–622 (1999)

    Article  CAS  Google Scholar 

  4. M.B. Gawande, V.D.B. Bonifacio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 5522–5551 (2013)

    Article  CAS  Google Scholar 

  5. C.-J. Li, L. Chen, Chem. Soc. Rev. 35, 68–82 (2006)

    Article  Google Scholar 

  6. J.B.F.N. Engberts, M.J. Blandamer, Chem. Commun, 1701–1708 (2001)

  7. J. Ge, J. Jiang, C. Yuan, C. Zhang, M. Liu, Tetrahedron Lett. 58, 1142–1145 (2017)

    Article  CAS  Google Scholar 

  8. H. Zhong, J. Wang, L. Li, R. Wang, Dalton Trans. 43, 2098–2103 (2014)

    Article  CAS  Google Scholar 

  9. S.M. Coman, V.I. Parvulescu, Org. Process Res. Dev. 19, 1327–1355 (2015)

    Article  CAS  Google Scholar 

  10. R. Martin, S.L. Buchwald, Acc. Chem. Res. 41, 1461–1473 (2008)

    Article  CAS  Google Scholar 

  11. B. Basu, K. Biswas, S. Kundu, S. Ghosh, Green Chem. 12, 1734–1738 (2010)

    Article  CAS  Google Scholar 

  12. S.J. Danishefsky, J.J. Masters, W.B. Young, J.T. Link, L.B. Snyder, T.V. Magee, D.K. Jung, R.C.A. Isaacs, W.G. Bornmann, C.A. Alaimo, C.A. Coburn, M.J. Di Grandi, J. Am. Chem. Soc. 118, 2843–2859 (1996)

    Article  CAS  Google Scholar 

  13. C.Y. Hong, N. Kado, L.E. Overman, J. Am. Chem. Soc. 115, 11028–11029 (1993)

    Article  CAS  Google Scholar 

  14. M. Karni, Y. Apeloig, J. Am. Chem. Soc. 112, 8589–8590 (1990)

    Article  CAS  Google Scholar 

  15. V.H. Rawal, S. Iwasa, J. Org. Chem. 59, 2685–2686 (1994)

    Article  CAS  Google Scholar 

  16. E. Doustkhah, S. Rostamnia, H.G. Hossieni, R. Luque, ChemistrySelect 2, 329–334 (2017)

    Article  CAS  Google Scholar 

  17. S. Rostamnia, H. Alamgholiloo, X. Liu, J. Colloid Interface Sci. 469, 310–317 (2016)

    Article  CAS  Google Scholar 

  18. S. Rostamnia, E. Doustkhah, B. Zeynizadeh, Microporous Mesoporous Mater. 222, 87–93 (2016)

    Article  CAS  Google Scholar 

  19. S. Rostamnia, H.G. Hossieni, E. Doustkhah, J. Organomet. Chem. 791, 18–23 (2015)

    Article  CAS  Google Scholar 

  20. U.M. Lindström, Organic Reactions in Water: Principles, Strategies and Applications (Blackwell, Hoboken, 2007)

    Book  Google Scholar 

  21. M. Shiri, M.A. Zolfigol, Tetrahedron 65, 587–598 (2009)

    Article  CAS  Google Scholar 

  22. J.S. Milano-Brusco, H. Nowothnick, M. Schwarze, R. Schomäcker, Ind. Eng. Chem. Res. 49, 1098–1104 (2010)

    Article  CAS  Google Scholar 

  23. G. La Sorella, G. Strukul, A. Scarso, Green Chem. 17, 644–683 (2015)

    Article  Google Scholar 

  24. C.C. Ruiz, J.A. Molina-Bolívar, J. Aguiar, G. MacIsaac, S. Moroze, R. Palepu, Langmuir 17, 6831–6840 (2001)

    Article  CAS  Google Scholar 

  25. B. Samiey, C.-H. Cheng, J. Wu, J. Chem. 2014, 14 (2014)

    Article  Google Scholar 

  26. T.K. Sau, A. Pal, N.R. Jana, Z.L. Wang, T. Pal, J. Nanopart. Res. 3, 257–261 (2001)

    Article  CAS  Google Scholar 

  27. A. Pal, S. Shah, S. Devi, Colloids and surfaces A: physicochem. Eng. Asp. 302, 483–487 (2007)

    Article  CAS  Google Scholar 

  28. G. Zhang, H. Zhou, J. Hu, M. Liu, Y. Kuang, Green Chem. 11, 1428–1432 (2009)

    Article  CAS  Google Scholar 

  29. B. Aswathy, S. Suji, G.S. Avadhani, R. Aswathy, S. Suganthi, G. Sony, J. Mol. Liq. 162, 155–158 (2011)

    Article  CAS  Google Scholar 

  30. A. Kumar, M.K. Gupta, M. Kumar, Tetrahedron Lett. 52, 4521–4525 (2011)

    Article  CAS  Google Scholar 

  31. J.-Z. Jiang, C. Cai, J. Colloid Interface Sci. 299, 938–943 (2006)

    Article  CAS  Google Scholar 

  32. D.S. Gaikwad, D.M. Pore, Synlett 23, 2631–2634 (2012)

    Article  CAS  Google Scholar 

  33. K. Ferré-Filmon, L. Delaude, A. Demonceau, A.F. Noels, Coord. Chem. Rev. 248, 2323–2336 (2004)

    Article  Google Scholar 

  34. S. Sengupta, S. Bhattacharyya, S. Kumar, Sadhukhan. J. Chem. Soc. Perkin Trans. 1, 275–278 (1998)

    Article  Google Scholar 

  35. L. Adak, S. Bhadra, B.C. Ranu, Tetrahedron Lett. 51, 3811–3814 (2010)

    Article  CAS  Google Scholar 

  36. I.P. Beletskaya, A.N. Kashin, A.E. Litvinov, V.S. Tyurin, P.M. Valetsky, G. van Koten, Organometallics 25, 154–158 (2006)

    Article  CAS  Google Scholar 

  37. J.-Z. Jiang, C. Cai, J. Colloid Interface Sci. 307, 300–303 (2007)

    Article  CAS  Google Scholar 

  38. K. Cheng, C. Wang, Y. Ding, Q. Song, C. Qi, X.-M. Zhang, J. Org. Chem. 76, 9261–9268 (2011)

    Article  CAS  Google Scholar 

  39. K. Kikukawa, T. Matsuda, Chem. Lett. 6, 159–162 (1977)

    Article  Google Scholar 

  40. J.G. Taylor, A.V. Moro, C.R.D. Correia, Eur. J. Org. Chem. 2011, 1403–1428 (2011)

    Article  Google Scholar 

  41. A. Roglans, A. Pla-Quintana, M. Moreno-Mañas, Chem. Rev. 106, 4622–4643 (2006)

    Article  CAS  Google Scholar 

  42. L. Wang, H. Li, P. Li, Tetrahedron 65, 364–368 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

One of authors DSG gratefully acknowledges Department of Science and Technology, New Delhi, India, for financial assistance under Start-up research Grant (No. SB/FT/CS-145/2014).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. S. Gaikwad.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 860 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gaikwad, D.S., Undale, K.A., Patil, D.B. et al. Triton X-100 stabilized Pd nanoparticles and their catalytic application in one-pot sequential Heck and Hiyama coupling in water. Res Chem Intermed 44, 265–275 (2018). https://doi.org/10.1007/s11164-017-3102-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-017-3102-5

Keywords

Navigation