Deaminative Fluorination of Anilines with Silicon Tetrafluoride: Utility of Silicon Tetrafluoride as a Fluorine Source

European Journal of Organic Chemistry

Volumn , Issue 4, 1998, Pages 725-727

  Tamura, Masanori ^a   Shibakami, Motonari ^a   Sekiya, Akira ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

Anilines; Deaminative fluorination; Fluorine; Fluoroarenes; Silicon

Indexed keywords

EID: 0041478512     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199804)1998:4<725::AID-EJOC725>3.0.CO;2-R     Document Type: Article

References (19)

1. Gmelin Handbook, Si Suppl., B7, p. 117.
2. Gmelin Handbook, Si Suppl., B7, pp. 244-248.
3. M. Shimizu, H. Yoshioka, Tetrahedron Lett. 1988, 29, 4101-4104.
4. M. Shimizu, H. Yoshioka, J. Chem. Soc., Chem. Commun. 1989, 1881-1882.
5. M. Tamura, M. Shibakami, S. Kurosawa, T. Arimura, A. Sekiya, J. Chem. Soc., Chem. Commun. 1995, 1891-1892.
6. M. Tamura, M. Shibakami, S. Kurosawa, T. Arimura, A. Sekiya, J. Fluorine Chem. 1996, 78, 95-96.
7. A. Roa, Org. React. 1949, 5, 193-228.
8. N. Yoneda, Tetrahedron 1991, 47, 5329-5365.
9. G. A. Olah, J. T. Welch, Y. D. Vanker, M. Nojima. I. Kerekes, J. A. Olah, J. Org. Chem. 1979, 44, 3872-3881.
10. T. Fukuhara, N. Yoneda, T. Sawada, A. Suzuki, Synth. Commun. 1987, 17, 685-692.
11. In relation to fluorination via arenediazonium ion, the C-F bond activation by aryl carbocations were recently reported; D. Ferraris, C. Cox, R. Anand, T. Lectka, J. Am. Chem Soc. 1997, 119, 4319-4320.
12. N. Yoneda, T. Fukuhara, Tetrahedron 1996, 52, 23-36.
13. Deaminative fluorination of p-cyanoaniline had not been reported. The yield in the reaction with pyridine-HF in Table 2 (entry 10, method B) is our experimental result.
14. R. H. Nettle, E. R. Roberts, D. W. Sharp, Spectrochim. Acta 1961, 17, 947-952.
15. P. H. Cheek, R. H. Willy, A. Roe, J. Am. Chem. Soc. 1949, 71, 1863.
16. S. Patai, The Chemistry of the Amino Group, John Wiley & Sons, 1968, p. 305-320.
17. S. Patai, The Chemistry of Diazonium and Diazo Groups, part 2, John Wiley & Sons, 1978, p. 514-520.
18. S. Oae, N. Asai, K. Fujimori, J. Chem. Soc., Perkin Trans. 2 1978, 1124-1130.
19. A. Sekiya, K. Ueda, Chem. Lett. 1990, 609-612.