New, practical and effective sources of fluoride ion for desilylation to form carbon anions

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2065-2068

  Busch Petersen, Jakob ^a   Bo, Yunxin ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY;

EID: 0033548472     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00166-5     Document Type: Article

References (19)

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2. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed.; Wiley, New York, 1991, p. 68.
3. (a) Paquette, L. A. ed. Encyclopedia of Reagents for Organic Synthesis; Wiley, New York, 1995, p. 4728.
4. (b) Yacobson, G. G.; Akhmetova, N. E. Synthesis 1983, 169.
5. (c) Kuwajima, I.; Nakamura, E. Accts. Chem. Res. 1985, 18, 181.
6. (d) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1983, 105, 1598.
7. Sharma, R. K.; Fry, J. L. J. Org. Chem. 1983, 48, 2112.
8. Seppelt, K. Angew. Chem. Int. Ed. Engl. 1992, 31, 292.
9. Christie, K. O.; Wilson, W. W.; Wilson, R. D.; Bau, R.; Feng, J. J. Am. Chem. Soc. 1990, 112, 7619.
10. Schwesinger, R.; Link, R.; Thiele, G.; Rotter, H.; Honert, D.; Limbach, H.-H.; Männle, F. Angew. Chem. Int. Ed. Engl. 1991, 30, 1372.
11. Gingras, M. Tetrahedron Lett. 1991, 33, 7381.
12. Pilcher, A. S.; DeShong P. J. Org. Chem. 1996, 61, 6901.
13. (a) Middleton, W. J. U.S. Patent 3,940,402, 1976.
14. (b) Noyori, R.; Nishida, I.; Sakata, J.; Nishizawa, M. J. Am. Chem. Soc. 1980, 102, 1223. (TASF= tris(diethylamino)sulfonium difluorotrimethylsilicate).
15. 2O: $0.93/g (Aldrich); CsCl: $0.46/g (Alfa); tris(dimethylamino)sulfonium difluorotrimethylsilicate: $24.8/g (Aldrich).
16. Anhydrous CsOH alone displayed very low activity.
17. 2O and HF).
18. 3): δδ 7.55 (d, J = 8.7 Hz, 2H), 7.49-7.45 (m, 2H), 7.34-7.31 (m, 3H), 6.93 (d, J = 8.7 Hz, 2H), 5.65 (s, 1H), 3.83 (s, 3H) ppm.
19. This research was supported by the National Science Foundation and the National Institutes of Health.