Cesium fluoride catalyzed trifluoromethylation of esters, aldehydes, and ketones with (trifluoromethyl)trimethylsilane

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2873-2876

  Singh, Rajendra P ^a   Cao, Ganfeng ^a   Kirchmeier, Robert L ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(TRIFLUOROMETHYL)TRIMETHYLSILANE; ALDEHYDE; CESIUM; CESIUM FLUORIDE; ESTER DERIVATIVE; KETONE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROLYSIS; METHYLATION;

EID: 0033574485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982494c     Document Type: Article

References (30)

1. Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393.
2. (a) Prakash, G, K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
3. (b) Farmham, W. B. In Synthetic Fluorine Chemistry; Olah, G. A., Chambers, R. D., Prakash, G. K. S., Eds.; John Wiley & Sons: New York, 1992; Chapter 11 and references therein.
4. (c) DesMarteau, D. D.; Xu, Z.; Witz, M. J. Org. Chem. 1992, 57, 629.
5. (d) Stefan, P. K.; Anderson, J. D. O.; DesMarteau, D. D. J. Org. Chem. 1992, 57, 1124.
6. Huang, D.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 3185.
7. Olah, G. A.; Chambers, R. D.; Prakash, G. K. S., Eds. Synthetic Fluorine Chemistry; John Wiley & Sons: New York, 1992.
8. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984.
9. Gelb, M. H.; Svaren, J. P.; Abales, R. H. Biochemistry 1985, 24, 1813.
10. Linderman, R. J.; Kirrolos, K. S. Tetrahedron Lett. 1989, 30, 2049.
11. Miyamura, M.; Watanabe, H. JP 78, 120, 528. Appl. 77/35, 706.; Chem. Abstr. 1979, 90, 160172u.
12. Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G. K. S.; Olah, G. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 820.
13. Patel, N. R.; Kirchmeier, R. L. Inorg. Chem. 1992, 31, 2537.
14. Tanner, D. D.; Gilberto, E. D.; Potter, A. J. Org. Chem. 1985, 50, 2149.
15. Sykes, A.; Tatlow, J. C.; Thomas, C. R. J. Chem. Soc. 1956, 835.
16. Aubert, C.; Begue, J. P.; Charpentier-Morize, M.; Nee, G.; Langlois, B. J. Fluorine Chem. 1989, 44, 161.
17. Ratner, V. G.; Pashkevich, K. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1996, 3, 680.
18. (a) Kitazume, T.; Sato, T. J. Fluorine Chem. 1985, 30, 189.
19. (b) Shen, Y.; Xin, Y.; Cen, W. Haung, Y. Synthesis 1984, 1, 35.
20. Sauer, D. T.; Shreeve, J. M. J. Fluorine Chem. 1971/72, 1, 1.
21. Gombler, W. Z. Naturforsch, B: Anorg, Chem., Org. Chem. 1981, 36B (5), 535.
22. Movchun, V. N.; Kolomeitsev, A. A.; Yagupolskii, Y. L. J. Fluorine Chem. 1995, 70, 255.
23. Hendrickson, J. B.; Bair, K. W. J. Org. Chem. 1977, 42, 3875.
24. Yu, S. L., Sauer, D. T.; Shreeve, J. M. Inorg. Chem. 1974, 13, 484.
25. Umemoto, T. Chem. Rev. 1996, 96, 1757.
26. Drabicky, M. J.; Myhre, P. C.; Reich, C. J., Schmittou, E. R. J. Org. Chem. 1976, 41, 1472.
27. (a) Fuchikami, T.; Hagiwara, T. Jpn. Kokai Tokyo Koho Jp 07, 118, 188 [95, 118, 188] (Cl. Co7C31/40).
28. (b) O'Reilly, M. J.; Maruta, M.; Ishikawa, N. Chem. Lett. 1984, 515.
29. Corley, R. S.; Cohen, S. G.; Simon, M. S.; Wolosinski, H. J. J. Am. Chem. Soc. 1958, 78, 2608.
30. Nelson, D. W.; O'Reilly, N. J.; Speier, J.; Gassman, P. G. J. Org. Chem. 1994, 59, 8157.