The 5 or 6 HF-Et3N Complex, Mild and Selective Hydrofluorination Agents for tert-Alkyl Fluorides

Synlett

Volumn 1996, Issue 6, 1996, Pages 529-530

  Hara, Shoji ^a   Kameoka, Mikio ^a   Yoneda, Norihiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000303011     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5499     Document Type: Article

References (17)

1. Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 779; Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 781; Olah, G. A., Welch, J. T., Vankar, Y. D., Nojima, M.; Kerekes, I.; Olah, J. A., J. Org. Chem. 1979, 44, 3872; Olah, G. A., Li, X.-Y., Synlett 1990, 267.
2. Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 779; Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 781; Olah, G. A., Welch, J. T., Vankar, Y. D., Nojima, M.; Kerekes, I.; Olah, J. A., J. Org. Chem. 1979, 44, 3872; Olah, G. A., Li, X.-Y., Synlett 1990, 267.
3. Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 779; Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 781; Olah, G. A., Welch, J. T., Vankar, Y. D., Nojima, M.; Kerekes, I.; Olah, J. A., J. Org. Chem. 1979, 44, 3872; Olah, G. A., Li, X.-Y., Synlett 1990, 267.
4. Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 779; Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 781; Olah, G. A., Welch, J. T., Vankar, Y. D., Nojima, M.; Kerekes, I.; Olah, J. A., J. Org. Chem. 1979, 44, 3872; Olah, G. A., Li, X.-Y., Synlett 1990, 267.
5. Yoneda, N.; Abe, T.; Fukuhara, T.; Suzuki, A. Chem. Lett. 1983, 1135; Yoneda, N.; Nagata, S.; Fukuhara, T.; Suzuki, A. Chem. Lett. 1984, 1241.
6. Yoneda, N.; Abe, T.; Fukuhara, T.; Suzuki, A. Chem. Lett. 1983, 1135; Yoneda, N.; Nagata, S.; Fukuhara, T.; Suzuki, A. Chem. Lett. 1984, 1241.
7. 4 was also shown to be effective for the hydrofluorination of simple olefins, see: Tamura, M.; Shibakami, M.; Kurosawa, S.; Arimura, T.; Sekiya, A. J. Chem. Soc., Chem. Commun. 1995, 1891.
8. Khrimian, A. P.; DeMilo, A. B.; Waters, R. M.; Liquido, N. J.; Nicholson. J. M. J. Org. Chem. 1994, 59, 8034.
9. Welch, J. T. Tetrahedron 1987, 43, 3123; Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991 and references cited therein.
10. Welch, J. T. Tetrahedron 1987, 43, 3123; Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991 and references cited therein.
11. McClinton, M. A. Aldrichimica Acta 1995, 28, 31 and references cited therein.
12. Yoneda, N.; Chen, S.-Q.; Hatakeyama, T.; Hara, S.; Fukuhara, T. Chem. Lett. 1994, 849; Hayashi, E.; Hara, S.; Shirato, H.; Hatakeyama, T.; Fukuhara, T.; Yoneda, N. Chem. Lett. 1995, 205; Hara, S.; Chen, S.-Q.; Hatakeyama, T.; Fukuhara, T.; Sekiguchi, M.; Yoneda, N. Tetrahedron Lett. 1995, 36, 6511.
13. Yoneda, N.; Chen, S.-Q.; Hatakeyama, T.; Hara, S.; Fukuhara, T. Chem. Lett. 1994, 849; Hayashi, E.; Hara, S.; Shirato, H.; Hatakeyama, T.; Fukuhara, T.; Yoneda, N. Chem. Lett. 1995, 205; Hara, S.; Chen, S.-Q.; Hatakeyama, T.; Fukuhara, T.; Sekiguchi, M.; Yoneda, N. Tetrahedron Lett. 1995, 36, 6511.
14. Yoneda, N.; Chen, S.-Q.; Hatakeyama, T.; Hara, S.; Fukuhara, T. Chem. Lett. 1994, 849; Hayashi, E.; Hara, S.; Shirato, H.; Hatakeyama, T.; Fukuhara, T.; Yoneda, N. Chem. Lett. 1995, 205; Hara, S.; Chen, S.-Q.; Hatakeyama, T.; Fukuhara, T.; Sekiguchi, M.; Yoneda, N. Tetrahedron Lett. 1995, 36, 6511.
15. A teflon bottle for centrifuge was used as the reaction vessel and during the reaction, the cap was tightly closed.
16. After the neutralization, the reaction mixture can be handled in glasswares.
17. Hexafluoroisopropanol was also effective in other cases to shorten the reaction time and as for the effect of this solvent, see: Ichikawa, J.; Miyazaki, S.; Fujiwara, M. Minami, T. J. Org. Chem. 1995, 60, 2320.