Synlett 2002(8): 1299-1301
DOI: 10.1055/s-2002-32965
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Fluorous Super Brønsted Acid Catalyst: Application to Fluorous Catalysis without Fluorous Solvents

Kazuaki Ishihara, Aiko Hasegawa, Hisashi Yamamoto*
Graduate School of Engineering, Nagoya University, SORST, Japan Science and Technology Corporation (JST), Furo-cho, Chikusa, Nagoya 464-8603, Japan
Fax: +81(52)7893222; e-Mail: yamamoto@cc.nagoya-u.ac.jp;
Weitere Informationen

Publikationsverlauf

Received 9 May 2002
Publikationsdatum:
25. Juli 2002 (online)

Abstract

The preparation of a fluorous super Brønsted acid catalyst, 4-(1H,1H-perfluorotetradecanoxy)-2,3,5,6-tetrafluorophenylbis(trifluoromethanesulfonyl)methane (3d), is described. The fluorous catalyst 3d can be recycled by using liquid/solid phase separation without fluorous solvents. A perfluorocarbon solvent is not essential for fluorous biphasic catalysis.

    References

  • 1a Horváth IT. Acc. Chem. Res.  1998,  31:  641 
  • 1b Cavazzini M. Montanari F. Pozzi G. Quici S. J. Fluorine Chem.  1999,  94:  183 
  • 1c Bhattacharyya P. Croxtall B. Fawcett J. Fawcett J. Gudmunsen D. Hope EG. Kemmitt RDW. Paige DR. Russell DR. Stuart AM. Wood DRW. J. Fluorine Chem.  2000,  101:  247 
  • 2 Ishihara K. Kondo S. Yamamoto H. Synlett  2001,  1371 
  • 3 Wende M. Meier R. Gladysz JA. J. Am. Chem. Soc.  2001,  123:  11490 
  • 4a Ishihara K. Hasegawa A. Yamamoto H. Angew. Chem. Int. Ed.  2001,  40:  4077 
  • 4b Ishihara K. Hasegawa A. Yamamoto H. Synlett  2002,  1296 
  • 5a Byron DJ. Matharu AS. Wilson RC. Liquid Crystals  1995,  19:  39 
  • 5b

    Pyridine was more effective as a solvent in the para-substitution reaction of a lithium salt of 1 with sodium alkoxides. In contrast, this reaction did not occur smoothly in diethyl ether, which was effective in the para-substitution reaction with alkyllithiums. [4]

  • 6 Rode BM. Engelbrecht A. Schantl JZ. J. Prakt. Chem.  1973,  253:  17 
  • 8 Barrett AGM. Braddock DC. Catterick D. Chadwick D. Henschke JP. McKinnell RM. Synlett  2000,  847 
  • 9 Mikami K. Mikami Y. Matsumoto Y. Nishikido J. Yamamoto F. Nakajima H. Tetrahedron Lett.  2001,  42:  289 
7

In the case of the esterification, the resultant solution was concentrated under reduced pressure, and the crude compounds were diluted in hexane to precipitate 3d. Thus, 3d was recovered by filtration.