Practically useful Reformatsky type reactions of chlorodifluoroacetate and bromodifluoroacetate induced by samarium(II) diiodide

Synthetic Communications

Volumn 26, Issue 13, 1996, Pages 2523-2529

  Yoshida, Masato ^a   Suzuki, Daiki ^a   Iyoda, Masahiko ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; FLUORINATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0030015049     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004565     Document Type: Article

References (18)

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3. Fürster, A., Synthesis, 1989, 571; Ishihara, I., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1992, 50, 347; Taguchi, T., Kitagawa, O., Suda, Y., Ohkawa, S., Hashimoto, A., Iitaka, Y., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 5291; Kitagawa, O., Taguchi, T., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 1803; Kitagawa, O., Hashimoto, A., Kobayashi, Y., and Taguchi, T., Chem. Lett., 1990, 1307; Burton, D. J. and Easdon, J. C., J. Fluorine Chem., 1988, 38, 125; Tukamoto, T., Yoshiyama, T., and Kitazume, T., Tetrahedron Asymmetry, 1991, 2, 759.
4. Fürster, A., Synthesis, 1989, 571; Ishihara, I., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1992, 50, 347; Taguchi, T., Kitagawa, O., Suda, Y., Ohkawa, S., Hashimoto, A., Iitaka, Y., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 5291; Kitagawa, O., Taguchi, T., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 1803; Kitagawa, O., Hashimoto, A., Kobayashi, Y., and Taguchi, T., Chem. Lett., 1990, 1307; Burton, D. J. and Easdon, J. C., J. Fluorine Chem., 1988, 38, 125; Tukamoto, T., Yoshiyama, T., and Kitazume, T., Tetrahedron Asymmetry, 1991, 2, 759.
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6. Fürster, A., Synthesis, 1989, 571; Ishihara, I., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1992, 50, 347; Taguchi, T., Kitagawa, O., Suda, Y., Ohkawa, S., Hashimoto, A., Iitaka, Y., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 5291; Kitagawa, O., Taguchi, T., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 1803; Kitagawa, O., Hashimoto, A., Kobayashi, Y., and Taguchi, T., Chem. Lett., 1990, 1307; Burton, D. J. and Easdon, J. C., J. Fluorine Chem., 1988, 38, 125; Tukamoto, T., Yoshiyama, T., and Kitazume, T., Tetrahedron Asymmetry, 1991, 2, 759.
7. Fürster, A., Synthesis, 1989, 571; Ishihara, I., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1992, 50, 347; Taguchi, T., Kitagawa, O., Suda, Y., Ohkawa, S., Hashimoto, A., Iitaka, Y., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 5291; Kitagawa, O., Taguchi, T., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 1803; Kitagawa, O., Hashimoto, A., Kobayashi, Y., and Taguchi, T., Chem. Lett., 1990, 1307; Burton, D. J. and Easdon, J. C., J. Fluorine Chem., 1988, 38, 125; Tukamoto, T., Yoshiyama, T., and Kitazume, T., Tetrahedron Asymmetry, 1991, 2, 759.
8. Fürster, A., Synthesis, 1989, 571; Ishihara, I., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1992, 50, 347; Taguchi, T., Kitagawa, O., Suda, Y., Ohkawa, S., Hashimoto, A., Iitaka, Y., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 5291; Kitagawa, O., Taguchi, T., and Kobayashi, Y., Tetrahedron Lett., 1988, 29, 1803; Kitagawa, O., Hashimoto, A., Kobayashi, Y., and Taguchi, T., Chem. Lett., 1990, 1307; Burton, D. J. and Easdon, J. C., J. Fluorine Chem., 1988, 38, 125; Tukamoto, T., Yoshiyama, T., and Kitazume, T., Tetrahedron Asymmetry, 1991, 2, 759.
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12. Samarium diiodide has been recognized to be an effective one-electron reducing reagent: Molander, G. A., Chem. Rev., 1992, 92, 29; Curran, D. P., Fevig, T. L., Jasperse, C. P., and Totleben, M. J., Synlett, 1992, 943; Soderquist, J. A., Aldrichimica Acta, 1991, 24, 5; Inanaga, J., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1989, 47, 200.
13. Samarium diiodide has been recognized to be an effective one-electron reducing reagent: Molander, G. A., Chem. Rev., 1992, 92, 29; Curran, D. P., Fevig, T. L., Jasperse, C. P., and Totleben, M. J., Synlett, 1992, 943; Soderquist, J. A., Aldrichimica Acta, 1991, 24, 5; Inanaga, J., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1989, 47, 200.
14. Samarium diiodide has been recognized to be an effective one-electron reducing reagent: Molander, G. A., Chem. Rev., 1992, 92, 29; Curran, D. P., Fevig, T. L., Jasperse, C. P., and Totleben, M. J., Synlett, 1992, 943; Soderquist, J. A., Aldrichimica Acta, 1991, 24, 5; Inanaga, J., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1989, 47, 200.
15. Samarium diiodide has been recognized to be an effective one-electron reducing reagent: Molander, G. A., Chem. Rev., 1992, 92, 29; Curran, D. P., Fevig, T. L., Jasperse, C. P., and Totleben, M. J., Synlett, 1992, 943; Soderquist, J. A., Aldrichimica Acta, 1991, 24, 5; Inanaga, J., Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1989, 47, 200.
16. Lang, R. W. and Schaub, B., Tetrahedron Lett., 1988, 29, 2943.
17. 2COOMe with aldehyde has been reported to take place efficiently in DMF: Shono, T., Kise, N., and Oka, H., Tetrahedron Lett., 1991, 32, 6577.
18. Imamoto, T. and Ono, M., Chem. Lett., 1987, 501.