Et3GeNa Promoted Formation of Trifluoromethyl Anion Species from C6H5SCF3: Effective Nucleophilic Trifluoromethylation of Various Aldehydes

Synlett

Volumn 1996, Issue 12, 1996, Pages 1191-1192

  Yokoyama, Yasuo ^a   Mochida, Kunio ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000747896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5720     Document Type: Article

References (28)

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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. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
4. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
5. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
6. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
7. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
8. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
9. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
10. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
11. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
12. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
13. For a review, see: Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992. For example, Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2948. Emeleus, H. J.; Haszeldine, R. N. J. Chem. Soc. 1949 2953. McBee, E. T.; Roberts, C. W.; Meiners, A. F. J. Am. Chem. Soc. 1957, 79, 335. Kobayashi, Y; Kumadaki, I. Tetrahedron Lett. 1969, 4095. Kobayashi, Y; Yamamoto, K; Kumadaki, I. Tetrahedron Lett. 1979, 4071. Kobayashi, Y.; Kumadaki, I. J. Chem. Soc. Perkin Trans. 1 1980, 661 and references cited therein. Kitazue, T; Ishikawa, N. Chem. Lett. 1981, 1679. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195. O'Neilly, N. J.; Maruta, M; Ishikawa, N. Chem. Lett. 1984, 517. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
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18. For example, Stahly, G. P.; Bell, D. R. J. Org. Chem. 1989, 54, 2873. Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393 and references cited therein. Urata, H; Fuchigami, T. Tetrahedron Lett. 1991, 32. 91 and references cited therein. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984. Prakash, G. K. S.; Yudin, A. K.; Deffieux, D.; Olah G. A. Synlett 1996, 151.
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22. FLUOROCHEM LTD.
23. 3Li readily decomposed to difluorocarbene in other reaction conditions. See: Pierce, O. R.; McBee, E. T.; Judd, G. F. J. Am. Chem. Soc. 1954, 76, 474.
24. 2 by use of NaOMe in HMPA. See: Sakurai, H.; Okada, A.; Kira, M.; Yonezawa, K. Tetrahedron Lett. 1971, 1511.
25. Stannyl anion species promoted reductive metallation of thiophenyl compounds was already reported. See: Takeda, T.; Ando, K.; Fujiwara, T. Chem. Lett. 1985, 1149.
26. Screttas, C. G.; Screttas, M. M. J. Org. Chem. 1979, 44, 713.
27. Bulten E. J.; Noltes J. G. Tetrahedron Lett. 1966, 4389. Bulten E. J.; Noltes J. G. Tetrahedron Lett. 1967, 1443.
28. Bulten E. J.; Noltes J. G. Tetrahedron Lett. 1966, 4389. Bulten E. J.; Noltes J. G. Tetrahedron Lett. 1967, 1443.