Chemoselective Trifluoromethylation of Methyl Esters Using an Et3GeNa/C6H5SCF3 Combination: Efficient Synthesis of Trifluoromethyl Ketones

Synlett

Volumn 1997, Issue 8, 1997, Pages 907-908

  Yokoyama, Yasuo ^a   Mochida, Kunio ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003191954     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-961     Document Type: Article

References (26)

1. Liebman, J. K.; Greenberg, A; Dolbier, Jr., W. R. Fluorine-containing Molecules, Structure, Reactivity, Synthesis; VCH: New York, 1988. Welch, J. T.; Eshwarakrishman, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
2. Liebman, J. K.; Greenberg, A; Dolbier, Jr., W. R. Fluorine-containing Molecules, Structure, Reactivity, Synthesis; VCH: New York, 1988. Welch, J. T.; Eshwarakrishman, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
3. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1913. Allen, K. N.; Abeles, R. H. Biochemistry 1989, 28, 8466. Brady, K.; Liang, T.-C.; Abeles, R. H. Biochemistry 1989, 28, 9066. Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
4. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1913. Allen, K. N.; Abeles, R. H. Biochemistry 1989, 28, 8466. Brady, K.; Liang, T.-C.; Abeles, R. H. Biochemistry 1989, 28, 9066. Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
5. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1913. Allen, K. N.; Abeles, R. H. Biochemistry 1989, 28, 8466. Brady, K.; Liang, T.-C.; Abeles, R. H. Biochemistry 1989, 28, 9066. Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
6. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1913. Allen, K. N.; Abeles, R. H. Biochemistry 1989, 28, 8466. Brady, K.; Liang, T.-C.; Abeles, R. H. Biochemistry 1989, 28, 9066. Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
7. Hammock, B. D.; Wing, K. D.; McLaughlin, J.; Lovell, V. M.; Sparks, T. C. Pestic. Biochem. Physiol. 1982, 17, 76. Hammock, B. D.; Abdel-Aal, Y. A. I.; Mullin, C. A.; Hanzlik, T. A.; Roe, R. M. Pestic. Biochem. Physiol. 1984, 22, 209. Ashour, M-B.; Hammock, B. D. Biochem. Pharmacol. 1987, 36, 1869.
8. Hammock, B. D.; Wing, K. D.; McLaughlin, J.; Lovell, V. M.; Sparks, T. C. Pestic. Biochem. Physiol. 1982, 17, 76. Hammock, B. D.; Abdel-Aal, Y. A. I.; Mullin, C. A.; Hanzlik, T. A.; Roe, R. M. Pestic. Biochem. Physiol. 1984, 22, 209. Ashour, M-B.; Hammock, B. D. Biochem. Pharmacol. 1987, 36, 1869.
9. Hammock, B. D.; Wing, K. D.; McLaughlin, J.; Lovell, V. M.; Sparks, T. C. Pestic. Biochem. Physiol. 1982, 17, 76. Hammock, B. D.; Abdel-Aal, Y. A. I.; Mullin, C. A.; Hanzlik, T. A.; Roe, R. M. Pestic. Biochem. Physiol. 1984, 22, 209. Ashour, M-B.; Hammock, B. D. Biochem. Pharmacol. 1987, 36, 1869.
10. For example, Nohira, H. J. Synth. Org. Chem. Jpn. 1991, 49, 467 and references cited therein.
11. Benayoud, F.; Bégué, J. P.; Bonnet-Delpon, D.; Fischer-Durand, N.; Sdassi, H. Synthesis 1993, 1083. Bégué, J. P.; Bonnet-Delpon, D.; Kornilov, A. Synthesis 1996, 529. For a review, see: Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron 1991, 47, 3207.
12. Benayoud, F.; Bégué, J. P.; Bonnet-Delpon, D.; Fischer-Durand, N.; Sdassi, H. Synthesis 1993, 1083. Bégué, J. P.; Bonnet-Delpon, D.; Kornilov, A. Synthesis 1996, 529. For a review, see: Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron 1991, 47, 3207.
13. Benayoud, F.; Bégué, J. P.; Bonnet-Delpon, D.; Fischer-Durand, N.; Sdassi, H. Synthesis 1993, 1083. Bégué, J. P.; Bonnet-Delpon, D.; Kornilov, A. Synthesis 1996, 529. For a review, see: Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron 1991, 47, 3207.
14. Nucleophilic trifluoromethylation of carboxylic esters using trifluoromethylmetallic reagent is difficult, but perfluoroalkylation by use of perfluoroalkylmetallic reagent is applicable for the effective formation of perfluoroalkyl ketones. See: McBee, E. T.; Roberts, C. W.; Curtis, S. G. J. Am. Chem. Soc. 1955, 77, 6387. Chen, L. S.; Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1984, 26, 341. Uno, H.; Shiraishi, Y.; Simokawa, K.; Suzuki, H. Chem. Lett. 1987, 1153. Uno, H.; Shiraishi, Y.; Suzuki, H. Bull. Chem. Soc. Jpn. 1989, 62, 2636. Uno, H.; Matsushima, Y.; Tasaka, T.; Suzuki, H. Bull Chem. Soc. Jpn. 1990, 63, 293.
15. Nucleophilic trifluoromethylation of carboxylic esters using trifluoromethylmetallic reagent is difficult, but perfluoroalkylation by use of perfluoroalkylmetallic reagent is applicable for the effective formation of perfluoroalkyl ketones. See: McBee, E. T.; Roberts, C. W.; Curtis, S. G. J. Am. Chem. Soc. 1955, 77, 6387. Chen, L. S.; Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1984, 26, 341. Uno, H.; Shiraishi, Y.; Simokawa, K.; Suzuki, H. Chem. Lett. 1987, 1153. Uno, H.; Shiraishi, Y.; Suzuki, H. Bull. Chem. Soc. Jpn. 1989, 62, 2636. Uno, H.; Matsushima, Y.; Tasaka, T.; Suzuki, H. Bull Chem. Soc. Jpn. 1990, 63, 293.
16. Nucleophilic trifluoromethylation of carboxylic esters using trifluoromethylmetallic reagent is difficult, but perfluoroalkylation by use of perfluoroalkylmetallic reagent is applicable for the effective formation of perfluoroalkyl ketones. See: McBee, E. T.; Roberts, C. W.; Curtis, S. G. J. Am. Chem. Soc. 1955, 77, 6387. Chen, L. S.; Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1984, 26, 341. Uno, H.; Shiraishi, Y.; Simokawa, K.; Suzuki, H. Chem. Lett. 1987, 1153. Uno, H.; Shiraishi, Y.; Suzuki, H. Bull. Chem. Soc. Jpn. 1989, 62, 2636. Uno, H.; Matsushima, Y.; Tasaka, T.; Suzuki, H. Bull Chem. Soc. Jpn. 1990, 63, 293.
17. Nucleophilic trifluoromethylation of carboxylic esters using trifluoromethylmetallic reagent is difficult, but perfluoroalkylation by use of perfluoroalkylmetallic reagent is applicable for the effective formation of perfluoroalkyl ketones. See: McBee, E. T.; Roberts, C. W.; Curtis, S. G. J. Am. Chem. Soc. 1955, 77, 6387. Chen, L. S.; Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1984, 26, 341. Uno, H.; Shiraishi, Y.; Simokawa, K.; Suzuki, H. Chem. Lett. 1987, 1153. Uno, H.; Shiraishi, Y.; Suzuki, H. Bull. Chem. Soc. Jpn. 1989, 62, 2636. Uno, H.; Matsushima, Y.; Tasaka, T.; Suzuki, H. Bull Chem. Soc. Jpn. 1990, 63, 293.
18. Nucleophilic trifluoromethylation of carboxylic esters using trifluoromethylmetallic reagent is difficult, but perfluoroalkylation by use of perfluoroalkylmetallic reagent is applicable for the effective formation of perfluoroalkyl ketones. See: McBee, E. T.; Roberts, C. W.; Curtis, S. G. J. Am. Chem. Soc. 1955, 77, 6387. Chen, L. S.; Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1984, 26, 341. Uno, H.; Shiraishi, Y.; Simokawa, K.; Suzuki, H. Chem. Lett. 1987, 1153. Uno, H.; Shiraishi, Y.; Suzuki, H. Bull. Chem. Soc. Jpn. 1989, 62, 2636. Uno, H.; Matsushima, Y.; Tasaka, T.; Suzuki, H. Bull Chem. Soc. Jpn. 1990, 63, 293.
19. Francése, C.; Tordeux, M.; Wakselman, C. Tetrahedron Lett. 1988, 29, 1029. Tordeux, M.; Francése, C.; Wakselman, C. J. Chem. Soc. Perkin I 1990, 1951 and references cited therein.
20. Francése, C.; Tordeux, M.; Wakselman, C. Tetrahedron Lett. 1988, 29, 1029. Tordeux, M.; Francése, C.; Wakselman, C. J. Chem. Soc. Perkin I 1990, 1951 and references cited therein.
21. Broicher, V.; Geffken, D. Tetrahedron Lett. 1989, 30, 5243. Broicher, V.; Geffken, D. Naturforsch, B: Chem. Ser. 1990, 45, 401.
22. Broicher, V.; Geffken, D. Tetrahedron Lett. 1989, 30, 5243. Broicher, V.; Geffken, D. Naturforsch, B: Chem. Ser. 1990, 45, 401.
23. Yokoyama, Y.; Mochida, K. Synlett 1996, 1991.
24. Yokoyama, Y.; Mochida, K. Tetrahedron Lett. in press.
25. Bulten, E. J.; Noltes, J. G. Tetrahedron Lett. 1966, 4389. Bulten, E. J.; Noltes, J. G. Tetrahedron Lett. 1967, 1443.
26. Bulten, E. J.; Noltes, J. G. Tetrahedron Lett. 1966, 4389. Bulten, E. J.; Noltes, J. G. Tetrahedron Lett. 1967, 1443.