Ytterbium(III) triflate-catalysed preparation of calix[4]resorcinarenes: Lewis assisted Brønsted acidity

Abstract

Calix[4]resorcinarenes 1–5 have been prepared in good yields by the ytterbium(III) triflate hydrate-catalysed condensation of equimolar amounts of aldehydes and resorcinol. The lanthanide salt was easily recovered and re-used following the reaction thus providing an atom economic synthesis of resorcinarenes. Evidence is presented that indicates that ytterbium(III) triflate can significantly increase the Brønsted  acidity of organic acids.

References

1. P. Timmerman, W. Verboom and D. N. Reinhoudt, Tetrahedron, 1996, 52, 2663.
2. A. G. S. Högberg, J. Org. Chem., 1980, 45, 4498.
3. A. G. S. Högberg, J. Am. Chem. Soc., 1980, 102, 6046.
4. L. Abis, E. Dalcanale, A. Du-vosel and S. Spera, J. Org. Chem., 1988, 53, 5475.
5. L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Weiser, J. A. Bryant, J. C. Sherman, R. C. Helgeson, C. B. Knobler and D. J. Cram, J. Org. Chem., 1989, 54, 1305.
6. S. Kobayashi and I. Hachiya, J. Org. Chem., 1994, 59, 3590.
7. A. Kawada, S. Mitamura and S. Kobayashi, Chem. Commun., 1996, 183.
8. A. G. M. Barrett and D. C. Braddock, Chem. Commun., 1997, 351.
9. F. J. Waller, A. G. M. Barrett, D. C. Braddock and D. Ramprasad, Chem. Commun., 1997, 613.
10. S. Kobayashi and H. Ishitani, J. Am. Chem. Soc., 1994, 116, 4083.
11. T. Saito, M. Kawamura and J.-I. Nishimura, Tetrahedron Lett., 1997, 38, 3231.
12. S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379.
13. S. Kobayashi, Synlett, 1994, 689.
14. J. H. Forsberg, V. T. Spaziano, T. M. Balasubramanian, G. K. Liu, S. A. Kinsley, C. A. Duckworth, J. J. Poteruca, P. S. Brown and J. L. Miller, J. Org. Chem., 1987, 52, 1017.
15. F. A. Hart, Scandium, Yttrium and the Lanthanides, ed. G. Wilkinson, Pergamon Press, Oxford, 1987, p. 1068.
16. J. C. F. Baes and R. E. Mesmer, The Hydrolysis of Cations, John Wiley and Sons, New York, 1976, p. 129.
17. S. Kobayashi, S. Nagayama and T. Busujima, J. Am. Chem. Soc., 1998, 120, 8287.
18. A. D. M. Curtis, Tetrahedron Lett., 1997, 38, 4295.
19. O. L. Pieroni, N. M. Rodriguez, B. M. Vuano and M. C. Cabaleiro, J. Chem. Res. (S), 1994, 188.
20. B. M. Trost, Angew. Chem., Int. Ed. Engl., 1995, 34, 259.
21. Y. Aoyama, Y. Tanaka and S. Sugahara, J. Am. Chem. Soc., 1989, 111, 5397.
22. H. Adams, F. Davis and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., 1994, 2527.
23. H. C. Brown and B. Kanner, J. Am. Chem. Soc., 1966, 88, 986.
24. F. J. Waller, D. Ramprasad, A. G. M. Barrett and D. C. Braddock, Catalysis of Organic Reactions, ed. F. E. Herkes, Marcel Dekker, Inc., New York, 1998, p. 289.
25. D. C. Braddock, presented in part at the 17th Conference on Catalysis of Organic Reactions, New Orleans, April, 1998.
26. F. J. Waller, A. G. M. Barrett, D. C. Braddock, R. M. McKinnell and D. Ramprasad, J. Chem. Soc., Perkin Trans. 1, preceding paper.
27. F. J. Waller, A. G. M. Barrett, D. C. Braddock and D. Ramprasad, Tetrahedron Lett., 1998, 39, 1641.
28. M. A. Ciufolini, M. V. Deaton, S. R. Zhu and M. Y. Chen, Tetrahedron, 1997, 53, 16299.
29. M. V. Deaton and M. A. Ciufolini, Tetrahedron Lett., 1993, 34, 2409.
30. A. Yanagisawa, K. Ishihara and H. Yamamoto, Synlett, 1997, 411.
31. H. C. Aspinall, N. Greeves and E. G. McIver, Tetrahedron Lett., 1998, 39, 9283.
32. V. J. Rao, D. L. Perlstein, R. J. Robbins, P. H. Lakshminarasimhan, H.-M. Kao, C. P. Grey and V. Ramamurthy, Chem. Commun., 1998, 269.
33. K. Murayama and K. Aoki, Chem. Commun., 1998, 607.
34. K. Aoki, personal communication.