Polymer-supported organic reactions: what takes place in the beads?

(Note: The full text of this document is currently only available in the PDF Version )

Philip Hodge


Abstract

The use of polymer-supported reactants in organic synthesis is currently of considerable interest, especially in the context of combinatorial syntheses. To carry out successfully reactions using polymer-supported reactants it is important to be aware of what takes place inside the beads. Examples are presented in this article which show that compared to the analogous homogeneous reactions systems, polymer-supported reactions can show substrate selectivity, be slower or faster, follow a different reaction course, or give a significantly different stereochemical result.


References

  1. R. B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149 Search PubMed.
  2. R. B. Merrifield, J. M. Stewart and N. Jernberg, Anal. Chem., 1966, 38, 1905 Search PubMed.
  3. B. Gutte and R. B. Merrifield, J. Biol. Chem., 1971, 246, 1922 Search PubMed.
  4. R. L. Letsinger and M. J. Kornet, J. Am. Chem. Soc., 1963, 85, 3045 Search PubMed.
  5. R. L. Letsinger and V. Mahadevan, J. Am. Chem. Soc., 1965, 87, 3526 Search PubMed; R. L. Letsinger and V. Mahadevan, J. Am. Chem. Soc., 1966, 88, 5319 Search PubMed.
  6. See, for example, N. K. Terrett, M. Gardner, D. W. Gordon, R. J. Kobylecki and J. Steele, Tetrahedron, 1995, 51, 8135 Search PubMed.
  7. G. Lowe, Chem. Soc. Rev., 1996, 25, 309 Search PubMed.
  8. W. Dumont, J. C. Poulin, T. P. Dang and H. B. Kagan, J. Am. Chem. Soc., 1973, 95, 8295 Search PubMed.
  9. N. Takaishi, H. Imai, C. A. Bertello and J. K. Stille, J. Am. Chem. Soc., 1976, 98, 5400 Search PubMed; N. Takaishi, H. Imai, C. A. Bertello and J. K. Stille, J. Am. Chem. Soc., 1978, 100, 264 Search PubMed.
  10. R. H. Grubbs and L. C. Kroll, J. Am. Chem. Soc., 1971, 93, 3062 Search PubMed.
  11. C. R. Harrison, P. Hodge, B. J. Hunt, E. Khoshdel and G. Richardson, J. Org. Chem., 1983, 48, 3721 Search PubMed.
  12. C. R. Harrison and P. Hodge, J. Chem. Soc. Perkin Trans. 1, 1982, 509 Search PubMed.
  13. D. W. Emerson, R. R. Emerson, S. C. Joshi, E. M. Sorensen and J. E. Turek, J. Org. Chem., 1979, 44, 4634 Search PubMed.
  14. T. Takagi, J. Appl. Pol. Sci., 1975, 19, 1649 Search PubMed.
  15. J. M. J. Frechet, M. D. de Smet and M. J. Farrall, J. Org. Chem., 1979, 44, 1774 Search PubMed.
  16. P. Hodge and J. Waterhouse, J. Chem. Soc. Perkin Trans. 1, 1983, 2319 Search PubMed.
  17. A. Guyot, P. Hodge, D. C. Sherrington and H. Widdecke, React. Polym., 1992, 16, 233 Search PubMed.
  18. M. Kempe and G. Barany, J. Am. Chem. Soc., 1996, 118, 7083 Search PubMed.
  19. J. M. Brown and J. A. Ramsden, Chem. Commun., 1996, 2117 Search PubMed.
  20. E. Bayer, Angew. Chem., 1991, 103, 117 Search PubMed.
  21. E. Atherton, R. C. Sheppard and A. J. Rosevar, J. Chem. Soc., Chem. Commun., 1981, 1151 Search PubMed.
  22. P. W. Small and D. C. Sherrington, J. Chem. Soc., Chem. Commun., 1989, 1589 Search PubMed.
  23. S. Itsuno, Y. Sakurai, K. Ito, T. Maruyama, S. Makahama and J. M. J. Fréchet, J. Org. Chem., 1990, 55, 304 Search PubMed.
  24. C. Yaroslavsky, A. Patchornik and E. Katchalski, Tetrahedron. Lett., 1970, 3629 Search PubMed.
  25. S. Kondo, S. Kawasoe, M. Ohira, T. Atarashi, K. Ikeda, H. Kunisada and Y. Yuki, Macromol. Rapid. Commun., 1995, 16, 291 Search PubMed.
  26. S. D. Alexandratos and D. H. J. Miller, Macromolecules, 1996, 29, 8025 Search PubMed.
  27. S. Mohanraj and W. T. Ford, Macromolecules, 1986, 19, 2470 Search PubMed.
  28. J. C. Briggs, P. Hodge and Z.-P. Zhang, React. Polym, 1993, 19, 73 Search PubMed.
  29. For an excellent review of the early work see W. T. Ford. in Polymeric Reagents and Catalysts, ed. W. T. Ford, ACS Symp. Ser. No. 308, Washington DC, 1986, ch. 11. Search PubMed.
  30. P. Hodge and E. Khoshdel, React. Polym., 1985, 3, 143 Search PubMed.
  31. R. H. Grubbs, G. Gibbons, L. C. Kroll, W. D. Bonds and C. H. Brubaker, J. Am. Chem. Soc., 1973, 95, 2373 Search PubMed.
  32. W. D. Bonds, C. H. Brubaker, E. S. Chandrasekaran, C. Gibbons, R. H. Grubbs and L. C. Kroll, J. Am. Chem. Soc., 1975, 97, 2128 Search PubMed.
  33. R. H. Grubbs, C. P. Lau, R. Cukier and C. H. Brubaker, J. Am. Chem. Soc., 1977, 99, 4517 Search PubMed.
  34. J. C. Briggs, P. Hodge and Z.-P. Zhang, Tetrahedron, 1997, 53, 3943 Search PubMed.
  35. M. Calmes, J. Daunis, H. Ismaili, R. Jacquier, J. Koudou, G. Nkusi and A. Zouanate, Tetrahedron, 1990, 46, 6021 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.