Highlights of applications in synthesis and catalysis: 10.18 liquid/solid catalyst-recycling method without fluorous solvents

Handbook of Fluorous Chemistry

Volumn , Issue , 2005, Pages 350-359

  Ishihara, Kazuaki ^a   Yamamoto, Hisashi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Fluorous catalysis without fluorous solvents; Fluorous chemistry; Liquid solid catalyst recycling method without fluorous solvents

Indexed keywords

CATALYSIS; CATALYSTS; RECYCLING;

CATALYST RECYCLING; FLUOROUS; FLUOROUS SOLVENTS;

SOLVENTS;

EID: 84958607524     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527603905.ch10r     Document Type: Chapter

References (20)

1. Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
2. Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183.
3. Bhattacharyya, P.; Croxtall, B.; Fawcett, J.; Fawcett, J.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M.; Wood, D. R. W. J. Fluorine Chem. 2000, 101, 247.
4. Ishihara, K.; Kondo, S.; Yamamoto, H. Synlett 2001, 1371.
5. Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490.
6. Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196.
7. Ishihara, K.; Yamamoto, H. Macromolecules 2000, 33, 3511.
8. Perfluorodecaline is not miscible with a non-fluorous solvent, toluene or o-xylene, even under reflux conditions.
9. For recent examples of precipitatable catalysts, see: Bergbreiter, D. E.; Koshti, N.; Franchina, J. G.; Frels, J. D. Angew. Chem., Int. Ed. Engl. 2000, 39, 1040.
10. Janda, K. D.; Reger, T. S. J. Am. Chem. Soc. 2000, 122, 6029.
11. Bosanac, T.; Yang, J.; Wilcox, C. S. Angew. Chem., Int. Ed. Engl. 2001, 40, 1875.
12. Ishihara, K.; Hasegawa, A.; Yamamoto, H. Synlett 2002, 1299.
13. Ishihara, K.; Hasegawa, A.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 2001, 40, 4077.
14. Ishihara, K.; Hasegawa, A.; Yamamoto, H. Synlett 2002, 1296.
15. Byron, D. J.; Matharu, A. S.; Wilson, R. C. Liq. Cryst. 1995, 19, 39. Pyridine is more effective as a solvent in the parasubstitution reaction of a lithium salt of 10 with sodium alkoxides. In contrast, this reaction does not occur smoothly in diethyl ether which is effective in the para-substitution reaction with alkyllithiums [8].
16. Rode, B. M.; Engelbrecht, A.; Schantl, J. Z. J. Prakt. Chem. (Leipzig) 1973, 253, 17.
17. In the case of the esterification, the resultant solution is concentrated under reduced pressure, and the crude compounds are diluted in hexane to precipitate 8. Thus, 8 is recovered by filtration.
18. Barrett, A. G. M.; Braddock, D. C.; Catterick, D.; Chadwick, D.; Henschke, J. P.; McKinnell, R. M. Synlett 2000, 847.
19. Mikami, K.; Mikami, Y.; Matsumoto, Y.; Nishikido, J.; Yamamoto, F.; Nakajima, H. Tetrahedron Lett. 2001, 42, 289.
20. Mikami, K.; Mikami, Y.; Matsuzawa, H.; Matsumoto, Y.; Nishikido, J.; Yamamoto, F.; Nakajima, H. Tetrahedron 2002, 58, 4015.