Development of new fluorination reaction using amine-nHF complexes as fluorine source

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 56, Issue 4, 1998, Pages 312-319

  Hara, Shoji ^a   Yoneda, Norihiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Electrochemical fluorination reactions; Et3N nHF complexes; Hydrofluorination; Nucleophilic fluorinating reagents; Oxidative fluorination

Indexed keywords

EID: 19044394958     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.56.312     Document Type: Article

References (40)

1. R. Franz. J. Fluorine Chem., 15, 423 (1980)
2. M.A. McClinton, Aldrichimica Acta, 28, 31 (1995);
3. G. Haufe, J. Prakt. Chem., 338, 99 (1996)
4. D. Boenigk. D. Mootz, J. Am. Chem. Soc., 110, 2135 (1988)
5. M.B. Giudicelli, D. Picq, B. Veyron, Tetrahedron Lett., 31, 6527 (1990)
6. (a) H. Suga, T. Hamatani, M. Schlosser, Tetrahedron, 6, 4247 (1990);
7. (b) J. Umezawa, O. Takahashi, K. Furuhashi, H. Nohira, Tetrahedron: Asymmetry, 4, 2053 (1993)
8. G.A. Olah, D. Meidar, Israel J. Chem., 17, 148 (1978)
9. C. Bonini, G. Righi, Synthesis, 1994, 225 ;
10. O.A. Mascaretti, Aldrichimica Acta, 26, 47 (1993)
11. A. Sattler, G. Haufe, J. Fluorine Chem., 69, 185 (1994)
12. S.-Q. Chen, T. Hatakeyama, T. Fukuhara, S. Hara, N. Yoneda, Electrochimica Acta, 42, 1951 (1997)
13. J.Y. Becker, L.L. Miller, T.M. Siegel, J. Am. Chem. Soc., 97, 849 (1975)
14. N. Yoneda, S.-Q. Chen, T. Hatakeyama, S. Hara, T. Fukuhara, Chem. Lett., 1994, 849
15. S. Hara, S.-Q. Chen, T. Hatakeyama, T. Fukuhara, M. Sekiguchi, N. Yoneda, Tetrahedron Lett., 36, 6511 (1995)
16. S. Hara, S.-Q. Chen, T. Hoshio, T. Fukuhara, N. Yoneda, Tetrahedron Lett., 37, 8511 (1996)
17. G.A. Olah, M. Nojima, I. Kerekes, Synthesis, 1973, 779 and 780;
18. G.A. Olah, J.T. Welch, Y. D. Vankar, M. Nojima, I. Kerekes, J.A. Olah, J. Ors. -Chem., 44, 3872 (1979);
19. G.A. Olah, X.-Y. Li, Synlett, 1990, 267
20. N. Yoneda, T. Abe, T. Fukuhara, A. Suzuki, Chem. Lett., 1983, 1135;
21. N. Yoneda, S. Nagata, T. Fukuhara, A. Suzuki, Chem. Lett., ibid., 1984, 1241
22. S. Hara, M. Kameoka, N. Yoneda, Synlett, 1996, 529
23. A.P. Khrimian, A.B. DeMilo, R.M. Waters, N.J. Liquido, J.M. Nicholson, J. Org. Chem., 59, 8034 (1994)
24. E. Hayashi, S. Kara, H. Shirato, T. Hatakeyama, T. Fukuhara, N. Yoneda, Chem. Lett., 1995, 205
25. J.T. Welch, S. Eswarakrishnan "Fluorine in Bioorganic Chemistry", John Wiley & Sons, New York (1991)
26. W. Carpenter, J. Org. Chem., 31, 2688 (1966)
27. M. Hudlicky, A. E. Pavlath, "Chemistry of Organic Fluorine Compounds II", American Chemical Society (1995)
28. S. Hara, M. Sekiguchi, A. Ohmori, T. Fukuhara, N. Yoneda, Chem. Commun., 1996, 1899
29. S. Hara, T. Hatakeyama, S.-Q. Chen, K. Ishii, M. Yoshida, M. Sawaguchi, T. Fukuhara, N. Yoneda, J. Fluorine Chem., 1997, in press
30. T. Fuchigami, T. Fujita, J. Org. Chem., 59, 7190 (1994)
31. A. Varvoglis, Synthesis, 1984, 709; 44, 660 (1986);
32. R. M. Moriarty, R.K. Vaid, Synthesis, 1990, 431;
33. R. M. Moriarty, R.K. Vaid, G.F. Koser, Synlett, 1990. 365; 53, 893 (1995)