Citation: Hong Chen, Zhi-Long Zou, Shi-Liang Tan, Jia-Hai Bi, De-Mei Tian, Hai-Bing Li. Efficient synthesis of water-soluble calix[4]arenes via thiol-ene “click” chemistry[J]. Chinese Chemical Letters, ;2013, 24(05): 367-369. shu

Efficient synthesis of water-soluble calix[4]arenes via thiol-ene “click” chemistry

  • Corresponding author: De-Mei Tian,  Hai-Bing Li, 
  • Received Date: 21 January 2013
    Available Online: 28 February 2013

  • Several water-soluble calix[4]arenes were synthesized via radical addition reaction between thiols and alkenes under UV lamp irradiation (λ= 365 nm) in good yields. The structures of these compounds synthesized herein were fully confirmed by 1H NMR, ESI-MS and elemental analysis.
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    1. [1]

      [1] (a) L. Mandolini, R. Ungaro, Calixarenes in Action, Imperial College Press, London, 2000;

    2. [2]

      (b) Z. Asfari, W. Bohmer, J. Harrowfield, et al., Calixarenes, Kluwer Academic Press, Dordrecht, 2001.

    3. [3]

      [2] (a) T. Nagasaki, K. Sisido, S. Shinkai, et al., Novel conformational isomerism of water-soluble calix[4]arenes, Tetrahedron 48 (1992) 797-804;

    4. [4]

      (b) S. Shimizu, K. Kito, C. Hirai, et al., Water-soluble calixarenes as new inverse phase-transfer catalysts. Nucleophilic substitution of alkyl and arylalkyl halides in aqueous media, Chem. Commun. (1997) 1629-1630.

    5. [5]

      [3] (a) A. Arduini, A. Pochini, R. Ungaro, p-t-Butyl-calix[4]arene tetracarboxylic acid. A water soluble calixarene in a cone structure, J. Chem. Soc. Chem. Commun. (1984) 981-982;

    6. [6]

      (b) C.D. Gutsche, I. Alam, Calixarenes. 23. The complexation and catalytic properties of water soluble calixarenes, Tetrahedron 44 (1988) 4689-4694.

    7. [7]

      [4] S. Shinkai, S. Mori, O. Mababe, et al., New water-soluble host molecules derived from calix[6]arene, Tetrahedron Lett. 25 (1984) 5315-5318.

    8. [8]

      [5] (a) A. Almi, A. Arduini, R. Ungaro, et al., Chloromethylation of calixarenes and synthesis of new water soluble macrocyclic hosts, Tetrahedron 45 (1989) 2177-2182;

    9. [9]

      (b) T. Arimura, T. Nagasaki, T. Matsuda, et al., Host-guest properties of new watersoluble calixarenes derived from p-(chloromethyl) calixarenes, J. Org. Chem. 54 (1989) 3766-3768.

    10. [10]

      [6] (a) A. Dondoni, A. Marra, R. Ungaro, et al., Synthesis and properties of O-glycosyl calix[4]arenes (calixsugars), Chem. Eur. J. 3 (1997) 1774-1782;

    11. [11]

      (b) R. Roy, J.M. Kim, Amphiphilic p-tert-butylcalix[4]arene scaffolds containing exposed carbohydrate dendrons, Angew. Chem. Int. Ed. 38 (1999) 369-372;

    12. [12]

      (c) G.M.L. Consoli, F. Cunsolo, V. Sgarlata, et al., Synthesis and lectin binding ability of glycosamino acid-calixarenes exposing GlcNAc clusters, Org. Lett. 6 (2004) 4163-4166.

    13. [13]

      [7] (a) Y. Hamuro, M.C. Calama, H.S. Park, et al., A calixarene with four peptide loops: an antibody mimic for recognition of protein surfaces, Angew. Chem. Int. Ed. Engl. 36 (1997) 2680-2683;

    14. [14]

      (b) H.S. Park, Q. Lin, A.D. Hamilton, Protein surface recognition by synthetic receptors: a route to novel submicromolar inhibitors for a-chymotrypsin, J. Am. Chem. Soc. 121 (1999) 8-13;

    15. [15]

      (c) A. Casnati, F. Sansone, R. Ungaro, Peptido-and glycocalixarenes: playing with hydrogen bonds around hydrophobic cavities, Acc. Chem. Res. 36 (2003) 246-254.

    16. [16]

      [8] (a) M. Kellermann, W. Bauer, C. Bottcher, et al., The first account of a structurally persistent micelle, Angew. Chem. Int. Ed. 43 (2004) 2959-2962;

    17. [17]

      (b) M. Lee, S.J. Lee, L.H. Jiang, Stimuli-responsive supramolecular nanocapsules from amphiphilic calixarene assembly, J. Am. Chem. Soc. 126 (2004) 12724-12725;

    18. [18]

      (c) E.H. Ryu, Y. Zhao, Environmentally responsive molecular baskets: unimolecular mimics of both micelles and reversed micelles, Org. Lett. 6 (2004) 3187-3189.

    19. [19]

      [9] H.C. Kolb, M.G. Finn, K.B. Sharpless, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed. 40 (2001) 2004-2021.

    20. [20]

      [10] W.G. Lewis, L.G. Green, K.B. Sharpless, et al., Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks, Angew. Chem. Int. Ed. 41 (2002) 1053-1057.

    21. [21]

      [11] (a) F. Fazio, M.C. Bryan, C.H. Wong, et al., Synthesis of sugar arrays in microtiter plate, J. Am. Chem. Soc. 124 (2002) 14397-14402;

    22. [22]

      (b) M.C. Bryan, F. Fazio, C.H. Wong, et al., Covalent display of oligosaccharide arrays in microtiter plates, J. Am. Chem. Soc. 126 (2004) 8640-8641;

    23. [23]

      (c) J.P. Collman, N.K. Devaraj, C.E.D. Chidsey, "Clicking" functionality onto electrode surfaces, Langmuir 20 (2004) 1051-1053.

    24. [24]

      [12] (a) P. Wu, A.K. Feldman, K.B. Sharpless, et al., Efficiency and fidelity in a clickchemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes, Angew. Chem. Int. Ed. 41 (2004) 3928-3932;

    25. [25]

      (b) B. Helms, J.L. Mynar, C.J. Hawker, et al., Dendronized linear polymers via "click chemistry", J. Am. Chem. Soc. 126 (2004) 15020-15021.

    26. [26]

      [13] C.R. Becer, R. Hoogenboom, U.S. Schubert, Click chemistry beyond metal-catalyzed cycloaddition, Angew. Chem. Int. Ed. 48 (2009) 4900-4908.

    27. [27]

      [14] V.V. Rostovtsev, L.G. Green, K.B. Sharpless, et al., A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes, Angew. Chem. Int. Ed. 41 (2002) 2596-2599.

    28. [28]

      [15] C.D. Gutsche, M. Iqbal, D. Stewart, Calixarenes. 19. Syntheses procedures for ptert-butylcalix[4]arene, J. Org. Chem. 51 (1986) 742-745.

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