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.
Similar content being viewed by others
References
H.H. Freedman, Pure Appl. Chem. 58, 857 (1986)
C.M. Starks, C.L. Liotta, Phase Transfer Catalysis, (Chapter 2) (Academic Press, NewYork, 1978)
W. Tagaki, I. Inoue, Y. Yano, T. Okonogi, Tetrahedron Lett. 15, 2587 (1974)
J. Dale, K. Daasvatn, Chem. Commun. 173, 295 (1976)
J.M. Lehn, Struct. Bond. 16, 1 (1973)
F. Montanari, P. Tundo, J. Org. Chem. 46, 2125 (1981)
J.P. Idoux, R. Wysocki Young, J. Turcot, C. Ohlmn, R. Leonard, Synth. Commun. 13, 137 (1983)
R. He, C. Ding, K. Maruoka, Angew. Chem. Int. Ed. 48, 4559 (2009)
C. Yildirim, C. Yolacan, F. Aydogan, Turk. J. Chem. 36, 101 (2012)
D. Enders, T.V. Nguyen, Org. Biomol. Chem. 10, 5327 (2012)
T. Balakrishnan, J.P. Jeyachandran, J. Chem. Soc. Perkin Trans. 2, 2081 (1995)
P. Srivastava, R. Srivatava, Tetrahedron Lett. 48, 4489 (2007)
H.E.S. Ali, Catal. Commun. 8, 855 (2007)
T. Balakrishnan, E. Murugan, A. Siva, Appl. Catal. A Gen. 273, 89 (2004)
L. Belding, P. Stoyanov, T. Dudding, J. Org. Chem. 81, 553 (2016)
M. Ranger, D. Rondeau, M. Leclerc, Macromolecules 30, 7686 (1997)
S.P. Dudek, M. Pouderoijen, R. Abbel, A.P.H.J. Schenning, E.W. Meijer, J. Am. Chem. Soc. 127, 11763 (2005)
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)
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)
M. Ghaemy, M. Barghamadi, J. Appl. Polym. Sci. 114, 3464 (2009)
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)
G. Saikia, P.K. Iyer, J. Org. Chem. 75, 2714 (2010)
Z. Ji, S. Li, Y. Li, W. Sun, Inorg. Chem. 49, 1337 (2010)
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)
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)
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)
S. Setthacheewakul, S. Mahattanadul, N. Phadoongsombut, W. Pichayakorn, Ruedeekorn Wiwattanapatapee. Eur. J. Pharm. Biopharm. 76, 475 (2010)
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)
A.N. Nurfinal, M.S. Reksohadiprodjo, H. Timmerman, U.A. Jenie, D. Sugiyant, H. van der Goot, Eur. J. Med. Chem. 32, 321 (1997)
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)
M.M. Yallapu, M. Jaggi, S.C. Chauhan, Drug Discov. Today 17, 71 (2012)
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)
S. Bisht, G. Feldmann, S. Soni, R. Ravi, C. Karikar, A. Maitra, A. Maitra, J. Nanobiotechnol. 5, 1 (2007)
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
L. Ding, S. Ma, H. Lou, L. Sun, M. Ji, Molecules 20, 21501 (2015)
D. Albanese, D. Landini, A. Maia, M. Penso, Ind. Eng. Chem. Res. 40, 2396 (2001)
T. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 46, 4222 (2007)
G. Pozzi, S. Quici, Richard H. Fish J. Fluor. Chem. 129, 920 (2008)
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).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-016-2600-1