Advertisement

Research on Chemical Intermediates

, Volume 42, Issue 12, pp 8345–8358 | Cite as

New quaternary phosphonium salt as multi-site phase-transfer catalyst for various alkylation reactions

  • Kottala Vijaya Ponmuthu
  • Duraimurugan Kumaraguru
  • Jesin Beneto Arockiam
  • Sadhasivam Velu
  • Murugesan Sepperumal
  • Siva Ayyanar
Article
  • 565 Downloads

Abstract

The present work describes the C-alkylation reactions of fluorene and curcumin catalyzed by a new phosphonium salt, benzene-1,3,5-triyltris(methylene))tris(triphenylphosphonium)bromide, as a multi-site phase-transfer catalyst (MPTC). The catalytic efficiencies were found to be quite effective for di- and tetra-alkylation reactions with very excellent yields under mild base and low concentrations of the catalyst. The synthesized MPTC 3 have privileged catalytic activity compared to commercially available single-site phase-transfer catalysts.

Keywords

Multi-site phase-transfer catalysts Homogeneous catalysis Fluorene Curcumin Tetraalkylation 

Notes

Acknowledgments

We acknowledge the financial support of the Department of Science and Technology, New Delhi, India (Grant No. SR/F/1584/2012-13), University Grants Commission, New Delhi, India (Grant No.UGC No.41-215/2012 (SR) and Council of Scientific and Industrial Research, New Delhi, India (Grant No. 01(2540)/11/EMR-II), DST-SERB, Extramural Major Research Project, New Delhi, India (Grant No. EMR/2015/000969).

Supplementary material

11164_2016_2600_MOESM1_ESM.docx (1.7 mb)
Supplementary material 1 (DOCX 1703 kb)

References

  1. 1.
    H.H. Freedman, Pure Appl. Chem. 58, 857 (1986)CrossRefGoogle Scholar
  2. 2.
    C.M. Starks, C.L. Liotta, Phase Transfer Catalysis, (Chapter 2) (Academic Press, NewYork, 1978)Google Scholar
  3. 3.
    W. Tagaki, I. Inoue, Y. Yano, T. Okonogi, Tetrahedron Lett. 15, 2587 (1974)CrossRefGoogle Scholar
  4. 4.
    J. Dale, K. Daasvatn, Chem. Commun. 173, 295 (1976)CrossRefGoogle Scholar
  5. 5.
    J.M. Lehn, Struct. Bond. 16, 1 (1973)CrossRefGoogle Scholar
  6. 6.
    F. Montanari, P. Tundo, J. Org. Chem. 46, 2125 (1981)CrossRefGoogle Scholar
  7. 7.
    J.P. Idoux, R. Wysocki Young, J. Turcot, C. Ohlmn, R. Leonard, Synth. Commun. 13, 137 (1983)CrossRefGoogle Scholar
  8. 8.
    R. He, C. Ding, K. Maruoka, Angew. Chem. Int. Ed. 48, 4559 (2009)CrossRefGoogle Scholar
  9. 9.
    C. Yildirim, C. Yolacan, F. Aydogan, Turk. J. Chem. 36, 101 (2012)Google Scholar
  10. 10.
    D. Enders, T.V. Nguyen, Org. Biomol. Chem. 10, 5327 (2012)CrossRefGoogle Scholar
  11. 11.
    T. Balakrishnan, J.P. Jeyachandran, J. Chem. Soc. Perkin Trans. 2, 2081 (1995)CrossRefGoogle Scholar
  12. 12.
    P. Srivastava, R. Srivatava, Tetrahedron Lett. 48, 4489 (2007)CrossRefGoogle Scholar
  13. 13.
    H.E.S. Ali, Catal. Commun. 8, 855 (2007)CrossRefGoogle Scholar
  14. 14.
    T. Balakrishnan, E. Murugan, A. Siva, Appl. Catal. A Gen. 273, 89 (2004)CrossRefGoogle Scholar
  15. 15.
    L. Belding, P. Stoyanov, T. Dudding, J. Org. Chem. 81, 553 (2016)CrossRefGoogle Scholar
  16. 16.
    M. Ranger, D. Rondeau, M. Leclerc, Macromolecules 30, 7686 (1997)CrossRefGoogle Scholar
  17. 17.
    S.P. Dudek, M. Pouderoijen, R. Abbel, A.P.H.J. Schenning, E.W. Meijer, J. Am. Chem. Soc. 127, 11763 (2005)CrossRefGoogle Scholar
  18. 18.
    S.J. Liu, Q. Zhao, Y. Deng, Y.J. Xia, J. Lin, Q.L. Fan, L.H. Wang, W. Huang, J. Phys. Chem. C 111, 1166 (2007)CrossRefGoogle Scholar
  19. 19.
    B. Pal, W.C. Yen, J.S. Yang, C.Y. Chao, Y.C. Hung, S.T. Lin, C.H. Chuang, C.W. Chen, W.F. Su, Macromolecules 41, 6664 (2008)CrossRefGoogle Scholar
  20. 20.
    M. Ghaemy, M. Barghamadi, J. Appl. Polym. Sci. 114, 3464 (2009)CrossRefGoogle Scholar
  21. 21.
    R. Abbel, C. Grenier, M.J. Pouderoijen, J.W. Stouwdam, P.E.L.G. Leclere, R.P. Sijbesma, E.W. Meijer, A.P.H.J. Schenning, J. Am. Chem. Soc. 131, 833 (2009)CrossRefGoogle Scholar
  22. 22.
    G. Saikia, P.K. Iyer, J. Org. Chem. 75, 2714 (2010)CrossRefGoogle Scholar
  23. 23.
    Z. Ji, S. Li, Y. Li, W. Sun, Inorg. Chem. 49, 1337 (2010)CrossRefGoogle Scholar
  24. 24.
    H. Ye, B. Zhao, M. Liu, X. Zhou, Y. Li, D. Li, S.J. Su, S.J. Su, W. Yang, Y. Cao, J. Mater. Chem. 21, 17454 (2011)CrossRefGoogle Scholar
  25. 25.
    S.J. Yoo, C.W. Jeon, J.J. Ha, S.Y. Nam, S.C. Shin, J. Hwang, Y.H. Kim, Macromol. Res. 21, 463 (2013)CrossRefGoogle Scholar
  26. 26.
    A. La Rosa, K. Gillemot, E. Leary, C. Evangeli, M. Teresa González, S. Filippone, G. Rubio-Bollinger, N. Agraït, C.J. Lambert, N. Martín, J. Org. Chem. 79, 4871 (2014)CrossRefGoogle Scholar
  27. 27.
    S. Setthacheewakul, S. Mahattanadul, N. Phadoongsombut, W. Pichayakorn, Ruedeekorn Wiwattanapatapee. Eur. J. Pharm. Biopharm. 76, 475 (2010)CrossRefGoogle Scholar
  28. 28.
    G. Liang, X. Li, L. Chen, S. Yang, X. Wu, E. Studer, E. Gurley, P.B. Hylemon, F. Ye, Y. Li, H. Zhou, Bioorg. Med. Chem. Lett. 18, 1525 (2008)CrossRefGoogle Scholar
  29. 29.
    A.N. Nurfinal, M.S. Reksohadiprodjo, H. Timmerman, U.A. Jenie, D. Sugiyant, H. van der Goot, Eur. J. Med. Chem. 32, 321 (1997)CrossRefGoogle Scholar
  30. 30.
    B.K. Adams, E.M. Ferstl, M.C. Davis, M. Herold, S. Kurtkaya, R.F. Camalier, M.G. Hollingshead, G. Kaur, E.A. Sausville, F.R. Rickles, J.P. Snyder, D.C. Liotta, M. Shoji, Bioorg. Med. Chem. 12, 3871 (2004)CrossRefGoogle Scholar
  31. 31.
    M.M. Yallapu, M. Jaggi, S.C. Chauhan, Drug Discov. Today 17, 71 (2012)CrossRefGoogle Scholar
  32. 32.
    D. Subramaniam, R. May, S.M. Sureban, K.B. Lee, R. George, P. Kuppusamy, R.P. Ramanujam, K. Hideg, B.K. Dieckgraefe, C.W. Houchen, S. Anant, Cancer Res 68, 1962 (2008)CrossRefGoogle Scholar
  33. 33.
    S. Bisht, G. Feldmann, S. Soni, R. Ravi, C. Karikar, A. Maitra, A. Maitra, J. Nanobiotechnol. 5, 1 (2007)CrossRefGoogle Scholar
  34. 34.
    M.T.A. Aziz, M.F. El-Asmar, A.M. Rezq, H.H. Fouad, H.H. Ahmed, A.A. Hassouna, F.M. Taha, H.F. Hafez, J. Cancer Ther. Res. (2012). doi: 10.7243/2049-7962-1-10 Google Scholar
  35. 35.
    L. Ding, S. Ma, H. Lou, L. Sun, M. Ji, Molecules 20, 21501 (2015)CrossRefGoogle Scholar
  36. 36.
    D. Albanese, D. Landini, A. Maia, M. Penso, Ind. Eng. Chem. Res. 40, 2396 (2001)CrossRefGoogle Scholar
  37. 37.
    T. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 46, 4222 (2007)CrossRefGoogle Scholar
  38. 38.
    G. Pozzi, S. Quici, Richard H. Fish J. Fluor. Chem. 129, 920 (2008)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  • Kottala Vijaya Ponmuthu
    • 1
  • Duraimurugan Kumaraguru
    • 1
  • Jesin Beneto Arockiam
    • 1
  • Sadhasivam Velu
    • 1
  • Murugesan Sepperumal
    • 1
  • Siva Ayyanar
    • 1
  1. 1.Department of Inorganic Chemistry, School of ChemistryMadurai Kamaraj UniversityMaduraiIndia

Personalised recommendations