Electrophilic fluorination of aromatics with selectfluor™ and trifluoromethanesulfonic acid 1

Israel Journal of Chemistry

Volumn 39, Issue 2, 1999, Pages 207-210

  Shamma, Tatyana ^a   Buchholz, Herwig ^a   Prakash, G K Surya ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033458491     PISSN: 00212148     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijch.199900026     Document Type: Article

References (37)

1. Electrophilic Aromatic Substitution. 65. Presented at the Organic Division, American Chemical Society, 212th National Meeting, Orlando, Florida, August 25-29, 1996, Paper No. 357. For 64, see: Olah, G.A.; Lee, C.S.; Prakash, G.K.S. J. Org. Chem. 1994, 59, 2590.
2. (a) Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982.
3. (b) Welch, J.T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry, Wiley: New York, 1991.
4. (c) Visser, G.W.M.; Bakker, C.N.M.; Halteren, B.W.v.; Herscheid, J.D.M.; Brinkman, G.A.; Hoekstra, A. J. Org. Chem. 1986, 51, 1886.
5. (d) Davis, F.A.; Han, W. Tetrahedron Lett. 1991, 1631.
6. (e) Zupan, M.; Stavber, S. J. Org. Chem. 1985, 50, 3609.
7. (f) Zupan, M.; Stavber, S.; Sotler, T. Tetrahedron Lett. 1994, 1105.
8. (g) Snieckus, V.; Beaulieu, F.; Mohri, K.; Han, W.; Murphy, C.K.; Davis, F.A. Tetrahedron Lett. 1994, 3465.
9. (a) Belanger, P.C.; Lau, C.K.; Williams, H.W.R.; Dufresne, C.; Scheigetz, J. Can. J. Chem. 1988, 66, 1479.
10. (b) Banks, R.E.; Mohialdin-Khaffaf, S.N.; Lal, G.S.; Sharif, L; Syvret, R.G. J. Chem. Soc., Chem. Commun. 1992, 595.
11. (c) Hodson, H.F.; Madge, D.J.; Slawin, A.N.Z.; Widdowson, D.A.; Williams, D.J. Tetrahedron 1994, 50, 1899.
12. (a) Balz, G.; Schiemann, G. Ber. Dtsch. Chem. Ges. B 1927, 60, 1186;
13. (b) Roe, A. Org. React. 1949, 5, 139.
14. (c) Suschitsky, H. Adv. Fluorine Chem. 1965, 4, 1.
15. (d) Fern, R.L.; Vanderwerf, C.A. J. Am. Chem. Soc. 1950, 72, 4809.
16. (e) Olah, G.A. and Li, X.-Y. "Fluorination with Onium Polyhydrogen Fluorides: The Taming of Anhydrous Hydrogen Fluoride for Synthesis". In Synthetic Fluorine Chemistry; Olah, G.A.; Chambers, R.D.; Prakash, G.K.S., Eds.; Wiley: New York, 1992; pp 163-204 and references cited therein.
17. Zupan, M.; Iskra, J.; Stavber, S. J. Fluorine Chem. 1995, 70, 7.
18. (a) Wilkinson, J.A. Chem. Rev. 1992, 92, 505.
19. (b) Rozen, S.; Lerman, O. J. Org. Chem. 1980, 45, 672.
20. (c) Olah, G.A.; Laali, K.; Farnia, M.; Singh, B.P.; Shack, J.C.; Christe, K.O. J. Org. Chem. 1985, 50, 1338.
21. Lal, G.S. J. Org. Chem. 1993, 58, 2791.
22. (a) Rozen, S.; Lerman, O.; Hebel, D.; Tor, Y. J. Org. Chem. 1984, 49, 806.
23. (b) Cacace, F.; Giacomello, P.; Wolf, A.P. J. Am. Chem. Soc. 1980, 102, 3511.
24. Taylor, E..; Bigham, E..; Johnson, D.K. J. Org. Chem. 1977, 42, 362.
25. (a) Lal, G.S.; Pez, G.P.; Syvret, R.G. Chem. Rev. 1996, 96, 1737.
26. (b) Schack, C.J.; Christe K.O. J. Fluorine Chem. 1981, 18, 363.
27. (a) Appelman, E.H.; Basile, L.J.; Hayatsu, R. Tetrahedron 1984, 40, 189.
28. (b) Zweig, A.; Fischer, R.G.; Lancaster, J.L. J. Org. Chem. 1980, 45, 3597.
29. (c) Patrick, T.B.; Darling, D.L. J. Org. Chem. 1986, 51, 3242.
30. Ip, D.; Arthur, C.D.; Winans, R.E.; Appleman, E.H. J. Am. Chem. Soc. 1981, 103, 1964-1968.
31. (a) Lal, G.S. J. Org. Chem. 1995, 60, 7340.
32. (b) Banks, R.E. J. Chem. Soc.. Chem. Commun. 1994, 343.
33. (c) Zupan, M.; Stavber, S. J. Chem. Soc., Chem. Commun. 1994, 149-150;
34. (d) Banks, R.E. J. Fluorine Chem. 1995, 73, 255.
35. (e) Banks, R.E. J. Fluorine Chem. 1998, 87, 1.
36. Singh, S.; DesMarteau, D.D.; Zuberi, S.S.; Witz, M.; Huang, Hsu-Nan J. Am. Chem. Soc. 1987, 109, 7194.
37. Appleman, E.H; Jache, A.W. J. Am. Chem. Soc. 1993, 115, 1376.