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

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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.

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References

  1. H.H. Freedman, Pure Appl. Chem. 58, 857 (1986)

    Article  CAS  Google Scholar 

  2. C.M. Starks, C.L. Liotta, Phase Transfer Catalysis, (Chapter 2) (Academic Press, NewYork, 1978)

    Google Scholar 

  3. W. Tagaki, I. Inoue, Y. Yano, T. Okonogi, Tetrahedron Lett. 15, 2587 (1974)

    Article  Google Scholar 

  4. J. Dale, K. Daasvatn, Chem. Commun. 173, 295 (1976)

    Article  Google Scholar 

  5. J.M. Lehn, Struct. Bond. 16, 1 (1973)

    Article  CAS  Google Scholar 

  6. F. Montanari, P. Tundo, J. Org. Chem. 46, 2125 (1981)

    Article  CAS  Google Scholar 

  7. J.P. Idoux, R. Wysocki Young, J. Turcot, C. Ohlmn, R. Leonard, Synth. Commun. 13, 137 (1983)

    Article  Google Scholar 

  8. R. He, C. Ding, K. Maruoka, Angew. Chem. Int. Ed. 48, 4559 (2009)

    Article  CAS  Google Scholar 

  9. C. Yildirim, C. Yolacan, F. Aydogan, Turk. J. Chem. 36, 101 (2012)

    CAS  Google Scholar 

  10. D. Enders, T.V. Nguyen, Org. Biomol. Chem. 10, 5327 (2012)

    Article  CAS  Google Scholar 

  11. T. Balakrishnan, J.P. Jeyachandran, J. Chem. Soc. Perkin Trans. 2, 2081 (1995)

    Article  Google Scholar 

  12. P. Srivastava, R. Srivatava, Tetrahedron Lett. 48, 4489 (2007)

    Article  CAS  Google Scholar 

  13. H.E.S. Ali, Catal. Commun. 8, 855 (2007)

    Article  CAS  Google Scholar 

  14. T. Balakrishnan, E. Murugan, A. Siva, Appl. Catal. A Gen. 273, 89 (2004)

    Article  CAS  Google Scholar 

  15. L. Belding, P. Stoyanov, T. Dudding, J. Org. Chem. 81, 553 (2016)

    Article  CAS  Google Scholar 

  16. M. Ranger, D. Rondeau, M. Leclerc, Macromolecules 30, 7686 (1997)

    Article  CAS  Google Scholar 

  17. S.P. Dudek, M. Pouderoijen, R. Abbel, A.P.H.J. Schenning, E.W. Meijer, J. Am. Chem. Soc. 127, 11763 (2005)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  20. M. Ghaemy, M. Barghamadi, J. Appl. Polym. Sci. 114, 3464 (2009)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  22. G. Saikia, P.K. Iyer, J. Org. Chem. 75, 2714 (2010)

    Article  CAS  Google Scholar 

  23. Z. Ji, S. Li, Y. Li, W. Sun, Inorg. Chem. 49, 1337 (2010)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  Google Scholar 

  27. S. Setthacheewakul, S. Mahattanadul, N. Phadoongsombut, W. Pichayakorn, Ruedeekorn Wiwattanapatapee. Eur. J. Pharm. Biopharm. 76, 475 (2010)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  31. M.M. Yallapu, M. Jaggi, S.C. Chauhan, Drug Discov. Today 17, 71 (2012)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  33. S. Bisht, G. Feldmann, S. Soni, R. Ravi, C. Karikar, A. Maitra, A. Maitra, J. Nanobiotechnol. 5, 1 (2007)

    Article  Google Scholar 

  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. L. Ding, S. Ma, H. Lou, L. Sun, M. Ji, Molecules 20, 21501 (2015)

    Article  CAS  Google Scholar 

  36. D. Albanese, D. Landini, A. Maia, M. Penso, Ind. Eng. Chem. Res. 40, 2396 (2001)

    Article  CAS  Google Scholar 

  37. T. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 46, 4222 (2007)

    Article  CAS  Google Scholar 

  38. G. Pozzi, S. Quici, Richard H. Fish J. Fluor. Chem. 129, 920 (2008)

    Article  CAS  Google Scholar 

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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).

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Correspondence to Siva Ayyanar.

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Ponmuthu, K.V., Kumaraguru, D., Arockiam, J.B. et al. New quaternary phosphonium salt as multi-site phase-transfer catalyst for various alkylation reactions. Res Chem Intermed 42, 8345–8358 (2016). https://doi.org/10.1007/s11164-016-2600-1

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  • DOI: https://doi.org/10.1007/s11164-016-2600-1

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