Fluorous Media

  • Tamejiro Hiyama
  • Hisashi Yamamoto
Chapter

Abstract

The isolation and purification of a desired organic compound after workup are inevitable but often tedious procedures. Thus, solid-phase synthesis [1] and phase-separation techniques [2] are introduced that allow isolation of the desired compounds in an almost pure form without such time-consuming procedures as column chromatography [3]. Very recently, in order to make the separation and purification of products and catalysts easier, PFCs have been introduced as solvents in organic synthesis.

Keywords

Aldehyde Alkene Porphyrin Ruthenium Transesterification 

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References

  1. 1.(a)
    N. C. Mathur, C. K. Narang, R. E. Williams, Polymers as Aids in Organic Chemistry, Academic Press, New York (1980)Google Scholar
  2. (b).
    L. M. Gayo, Biotechnol. Bioeng. (Combinatorial Chemistry) 1998, 61, 95CrossRefGoogle Scholar
  3. 2.(a)
    D. P. Curran, Angew. Chem. Int. Ed. Engl. 1998, 37, 1174CrossRefGoogle Scholar
  4. (b).
    B. Cornils, Angew. Chem. Int. Ed. Engl. 1995, 34, 1575CrossRefGoogle Scholar
  5. (c).
    I. T. Horvath, F. Joó, Eds., Aqueous Organometallic Chemistry and Catalysts, Kluwer, Dordrecht (1995)Google Scholar
  6. 3.(a)
    W. C. Still, M. Kahn, A. Mitra, J. Org. Chem., 1978, 43, 2923CrossRefGoogle Scholar
  7. (b).
    Y. Naruta, H. Uemori, M. Fukumoto, H. Sugiyama, Y. Sakata, K. Maruyama, Bull. Chem. Soc. Jpn., 1988, 61, 1815CrossRefGoogle Scholar
  8. 4.
    D.-W. Zhu, Synthesis 1993, 953Google Scholar
  9. 5.
    K. Tsubushi, Jpn. Kokai Tokkyo Koho JP 2–24362 [90–243602]Google Scholar
  10. 6.
    S. M. Pereira, G. P. Savage, G. W. Simpson, Synth. Commun. 1995, 25, 1023CrossRefGoogle Scholar
  11. 7.
    T. Nalkamura, A. Yabe, Chem. Lett. 1995, 533Google Scholar
  12. 8.
    I. Klement, P. Knochel, Synlett. 1995, 1113Google Scholar
  13. 9.
    R. D. Chambers, G. Sandford, A. Shah, Synth. Commun. 1996, 26, 1861CrossRefGoogle Scholar
  14. 10.
    A. Ogawa, D. P. Curran, J. Org. Chem. 1997, 62, 450CrossRefGoogle Scholar
  15. 11.(a)
    I. T. Horvath, J. Rabai, Science 1994, 266, 72CrossRefGoogle Scholar
  16. (b).
    I. T. Hovath, Acc. Chem. Res., 31, 61 (1998)CrossRefGoogle Scholar
  17. 12.
    A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf, D. P. Curran, Science 1997, 275, 823CrossRefGoogle Scholar
  18. 13.(a)
    J. A. Gladysz, Science 1994, 266, 55CrossRefGoogle Scholar
  19. (b).
    B. Cornils, Angew. Chem. Int. Ed. Engl. 1997, 36, 2057Google Scholar
  20. 14.
    E. G. Kuntz, Chemtech 1987, 17, 570Google Scholar
  21. 15.
    R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286CrossRefGoogle Scholar
  22. 16.
    I. T. Horvath, G. Kiss, R. A. Cook, J. E. Bond, P. A. Stevens, J. Rábai, E. J. Mozeleski, J. Am. Chem. Soc. 1998, 120, 3133CrossRefGoogle Scholar
  23. 17.
    C. Li, S. P. Nolan, I. T. Horváth, Organometallics 1998, 17, 452CrossRefGoogle Scholar
  24. 18.
    J. Fawcett, E. G. Hope, R. D. W. Kemmitt, D. R. Paige, D. R. Russell, A. M. Stuart, D. J. Cole-Hamilton, M. J. Payne, Chem. Commun. 1997, 1127Google Scholar
  25. 19.
    M.-A. Guillevic, A. M. Arif, I. T. Horvath, Angew. Chem. Int. Ed. Engl. 1997, 36, 1612CrossRefGoogle Scholar
  26. 20.
    M.-A. Guillevic, C. Rocaboy, A. M. Arif, I. T. Horvath, J. A. Gladysz, Organometallics 1998, 17, 707CrossRefGoogle Scholar
  27. 21.
    J. J. J. Juliette, I. T. Horvath, J. A. Gladysz, Angew. Chem. Int. Ed. Engl. 1997, 36, 1610CrossRefGoogle Scholar
  28. 22.
    I. Klement, H. Lütjens, P Knochel, Angew. Chem. Int. Ed. Engl. 1997, 36, 1454CrossRefGoogle Scholar
  29. 23.
    T. Yamada, T. Takai, O. Rhode, T. Mukaiyama, Chem. Lett. 1991, 1Google Scholar
  30. 24.
    G. Pozzi, S. Banfi, A. Manfredi, F. Montanari, S. Quici, Tetrahedron 1996, 52, 1 1879Google Scholar
  31. 25.
    G. Pozzi, F. Montanari, S. Quici, Chem. Commun. 1997, 69Google Scholar
  32. 26.
    G. Pozzi, E Cinato, F. Montanari, S. Quici, Chem. Commun. 1998, 877Google Scholar
  33. 27.
    Epoxidation of alkenes using manganese(III) acetate dihydrate in perfluoro-2-butyltetrahydrofuran or perfluoropropanol: K. S. Ravikumar, E Barbier, J.-P. Bégué, D. BonnetDelpon, Tetrahedron 1998, 54, 7457Google Scholar
  34. 28.(a)
    T. Yamada, K. Imagawa, T. Nagata, T. Mukaiyama, Chem. Lett. 1992, 2231Google Scholar
  35. (b).
    K. Imagawa, T. Nagata, T. Yamada, T. Mukaiyama, Chem. Lett. 1994, 527Google Scholar
  36. 29.
    G. Pozzi, M. Cavazzini, S. Quici, S. Fontana, Tetrahedron Lett. 1997, 38, 7605CrossRefGoogle Scholar
  37. 30.
    J.-M. Vincent, A. Rabion, V. K. Yachandra, R. H. Fish, Angew. Chem. Int. Ed. Engl. 1997, 36, 2346CrossRefGoogle Scholar
  38. 31.
    S. G. DiMagno, P. H. Dussault, J. A. Schultz, J. Am. Chem. Soc. 1996, 118, 5312CrossRefGoogle Scholar
  39. 32.
    S. G. DiMagno, R. A. Williams, M. J. Therien, J. Org. Chem. 1994, 59, 6943CrossRefGoogle Scholar
  40. 33.
    A. Studer, P. Jeger, P. Wipf, D. P. Curran, J. Org. Chem. 1997, 62, 2917Google Scholar
  41. 34.
    D. P. Curran, R. Ferritto, Y. Hua, Tetrahedron Lett. 1998, 39, 4937CrossRefGoogle Scholar
  42. 35.
    D. Crich, S. Sun, J. Org. Chem. 1996, 61, 7200CrossRefGoogle Scholar
  43. 36.
    D. P. Curran, S. Hadida, J. Am. Chem. Soc. 1996, 118, 2531CrossRefGoogle Scholar
  44. 37.
    D. P. Curran, S. Hadida, M. He, J. Org.Chem. 1997, 62, 6714CrossRefGoogle Scholar
  45. 38.
    D. P. Curran, M. Hoshino, J. Org.Chem. 1996, 61, 6480CrossRefGoogle Scholar
  46. 39.
    M. Hoshino, P. Degenkolb, D. P. Curran, J. Org.Chem. 1997, 62, 8341CrossRefGoogle Scholar
  47. 40.
    M. Larhed, M. Hoshino, S. Hadida, D. P. Curran, A. Hallberg, J. Org.Chem. 1997, 62, 5583CrossRefGoogle Scholar
  48. 41.
    S. Hadida, M. S. Super, E. J. Beckman, D. P. Curran, J. Am. Chem. Soc. 1997, 119, 7406CrossRefGoogle Scholar
  49. 42.
    N. Spetseris, S. Hadida, D. P. Curran, T. Y. Meyer, Organometallics, 1998, 17, 1458CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Tamejiro Hiyama
    • 1
  • Hisashi Yamamoto
    • 2
  1. 1.Department of Material Chemistry, Graduate School of EngineeringKyoto UniversityKyotoJapan
  2. 2.Graduate School of EngineeringNagoya UniversityNagoyaJapan

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