Fluorous phase separation techniques in catalysis

Abstract

Fluorous solvents have limited miscibility with conventional organic solvents. Combined with the fact that compounds functionalized with perfluorinated groups often dissolve preferentially in fluorous solvents this can be used to extract fluorous components from reaction mixtures. This review discusses the application and potential of fluorous phase separation techniques for the recovery of soluble metal catalysts.

References

1. D. W. Zhu, Synthesis, 1993, 953.
2. L. A. Halper, C. O. Timmons and W. A. Zisman, J. Colloid Interface Sci., 1972, 38, 511.
3. J. G. Riess and M. Le Blanc, Pure Appl. Chem., 1982, 54, 2383 and references cited therein.
4. C. Tamborski, C. E. Snijder and J. B. Christian, US Patent 4454349, 1984; Chem. Abstr., 1984, 101, 152079z.
5. P. Smith and K. H. Gardner, Macromolecules, 1985, 18, 1222 and references cited therein.
6. K. Lorenz, H. Frey, B. Stühn and R. Mülhaupt, Macromolecules, 1997, 30, 6860.
7. R. Banga and J. Yarwood, Langmuir, 1995, 11, 4393.
8. R. K. Kobos, J. W. Eveleigh and R. Arentzen, Trends Biotechnol., 1989, 7, 101.
9. T. H. Maugh, Science, 1979, 206, 205.
10. I. T. Horváth and J. Rábai, Science, 1994, 266, 72.
11. B. Cornils, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036.
12. R. P. Hughes, Adv. Organomet. Chem., 1990, 31, 183.
13. M. G. L. Petrucci and A. K. Kakkar, Advan. Mater., 1996, 8, 251 and references cited therein.
14. J. W. Knapen, A. W. van der Made, J. C. Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove and G. van Koten, Nature, 1994, 372, 659.
15. W. A. Hermann and C. W. Kohlpaintner, Angew. Chem., Int. Ed. Engl., 1993, 32, 1524.
16. D. P. Curran, Angew. Chem., Int. Ed. Engl., 1998, 37, 1174 and references cited therein.
17. R. P. Hughes and H. A. Trujillo, Organometallics, 1996, 15, 286.
18. J. E. Huheey, J. Phys. Chem., 1965, 69, 3284.
19. T. Umemoto, Chem. Rev., 1996, 96, 1757.
20. J. G. Goll, K. T. Moore, A. Ghosh and M. J. Therien, J. Am. Chem. Soc., 1996, 118, 8344.
21. H. Kleijn, J. T. B. H. Jastrzebski, R. A. Gossage, H. Kooijman, A. L. Spek and G. van Koten, Tetrahedron, 1998, 54, 1145.
22. I. T. Horváth, G. Kiss, R. A. Cook, J. E. Bond, P. A. Stevens, J. Rábai and E. J. Mozeliski, J. Am. Chem. Soc., 1998, 120, 3133.
23. J. Fawcett, E. G. Hope, R. D. W. Kemmitt, D. R. Paige, D. R. Russell, A. M. Stuart, D. J. Cole-Hamilton and M. J. Payne, Chem. Commun., 1997, 1127.
24. M. A. Guillevic, C. Rocaboy, A. M. Arif, I. T. Horváth and J. A. Gladysz, Organometallics, 1998, 17, 707.
25. J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, Angew. Chem., Int. Ed. Engl., 1997, 36, 1610.
26. G. Pozzi, F. Monatari and S. Quici, Chem. Commun., 1997, 69.
27. G. Pozzi, J. Colombani, M. Miglioli, F. Monatari and S. Quici, Tetrahedron, 1997, 52, 6145.
28. G. Pozzi, M. Cavazzini and S. Quici, Tetrahedron Lett., 1997, 38, 7605.
29. J.-M. Vincent, A. Rabion, V. K. Yachandra and R. H. Fish, Angew. Chem., Int. Ed. Engl., 1997, 36, 2346.
30. I. Klement, H. Lütjens and P. Knochel, Angew. Chem., Int. Ed. Engl., 1997, 36, 1454.
31. B. Betzemeier and P. Knochel, Angew. Chem., Int. Ed. Engl., 1997, 36, 2623.
32. D. E. Bergreiter and J. G. Franchina, Chem. Commun., 1997, 1531.
33. S. Kainz, D. Koch, W. Baumann and W. Leitner, Angew. Chem., Int. Ed. Engl., 1997, 36, 1628.
34. B. E. Smart, in The Chemistry of Functional Groups, Supplement D, eds. S. Patai and Z. Rappoport, John Wiley & Sons Ltd., Chichester, 1983, pp. 603–653.
35. R. L. Scott, J. Phys. Chem., 1958, 62, 136 and references cited therein.
36. P. Lo Nostro, Adv. Colloid Interface Sci., 1995, 56, 245 and references cited therein.
37. H. Ding, B. E. Hanson, T. Bartik and B. Bartik, Organometallics, 1994, 13, 3761.
38. G. Oehme, E. Paetzold and R. Selke, J. Mol. Catal., 1992, 71, L1.
39. W. Guo, T. A. Brown and B. M. Fung, J. Phys. Chem., 1991, 95, 1829.