The role of F-N reagent and reaction conditions on fluoro functionalisation of substituted phenols

Tetrahedron

Volumn 62, Issue 18, 2006, Pages 4474-4481

  Pravst, Igor ^a   Iskra, Maja Papež ^a   Jereb, Marjan ^a   Zupan, Marko ^a,b   Stavber, Stojan ^b  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

F N reagents; Fluorination; Kinetics; Selectfluor F TEDA BF4; Solvent effects; Substituent effects; Substituted phenols

Indexed keywords

2 FLUORO 4 (1,1,3,3 TETRAMETHYLBUTYL)PHENOL; 2 FLUORO 4 ISOPROPYLPHENOL; 2 FLUORO 4 METHYLPHENOL; 2 FLUORO 4 TERT BUTYLPHENOL; 4 FLUORO 4 ISOPROPYLCYCLOHEXA 2,5 DIENONE; 4 FLUORO 4 METHYLCYCLOHEXA 2,5 DIENONE; 4 FLUOROPHENOL; 4 TERT BUTYL 4 FLUOROCYCLOHEXA 2,5 DIENONE; FLUORINE; FLUORINE DERIVATIVE; NITROGEN; PHENOL DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ALKYLATION; ANALYTIC METHOD; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CORRELATION COEFFICIENT; DEMETHYLATION; FLUORINATION; OXIDATION; PRIORITY JOURNAL;

EID: 33646079653     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.051     Document Type: Article

References (39)

1. Rappoport Z. The Chemistry of Phenols. Part 1 (2003), Wiley, Chichester
2. Patai S., and Rappoport Z. The Chemistry of Phenols. Part 2 (2003), Wiley, Chichester
3. Filler R., Kobayashi Y., and Yagupolskii L.M. Organofluorine Compounds in Medicinal Chemistry and Biological Applications (1993), Elsevier, Amsterdam
4. Filler R., and Kobayashi Y. Biomedical Aspects of Fluorine Chemistry (1982), Elsevier, Amsterdam
5. Welch J.T., and Eswarakrishanan S. Fluorine in Bioorganic Chemistry (1991), Wiley, Canada
6. Patani G.A., and Lavoie E.J. Chem. Rev. 96 (1996) 3147-3176
7. Tius M.A. Tetrahedron 24 (1995) 6605-6634
8. Wilkinson J.A. Chem. Rev. 92 (1992) 505-519
9. Rozen S. In: Patai S., and Rappoport Z. (Eds). The Formation of the C-F Bond: The Last Twelve Years. The Chemistry of Functional Groups, Supplement D2: The Chemistry of Halides, Psevdo-Halides and Azides, Part 1 and 2 (1995), Wiley, Chichester 629-708
10. Rozen S. Chem. Rev. 96 (1996) 1717-1736
11. Zupan M. In: Patai S., and Rappoport Z. (Eds). Functionalization of Organic Molecules by Xenon Fluorides. The Chemistry of Functional Groups, Supplement D2: The Chemistry of Halides, Psevdo-Halides and Azides. Part 1 and 2 (1995), Wiley, Chichester 821-860
12. In: German L., and Zemskov S. (Eds). New Fluorinating Agents in Organic Synthesis (1989), Springer, Berlin
13. In: Baasner B., Hagenann H., and Tatlow J.C. (Eds). Methods in Organic Chemistry (Hauben-Weyl). Organo-fluorine Compounds Vol. E 10a (1999), Thieme, Stuttgart
14. Chambers R.D. Fluorine in Organic Chemistry (2004), Blackwell, Oxford
15. Lal G.S., Pez G.P., and Syvret R.G. Chem. Rev. 96 (1996) 1737-1755
16. Banks R.B. J. Fluorine Chem. 87 (1998) 1-17
17. Taylor S.D., Kotoris C.C., and Hum G. Tetrahedron 55 (1999) 12431-12477
18. Furin G.G., and Fainzilberg A.A. Russ. Chem. Rev. 68 (1999) 653-684
19. Singh R.P., and Shreeve J.M. Acc. Chem. Res. 37 (2004) 31-44
20. Nyffeler P.T., Durón S.G., Burkart M.D., Vincent S.P., and Wong C.H. Angew. Chem., Int. Ed. 44 (2005) 192-212
21. Stavber S., and Zupan M. Acta Chim. Slov. 52 (2005) 13-26
22. Stavber S., and Zupan M. In: Rahman A., and Laali K.K. (Eds). N-Fluoro-diazonia-bicyclo[2.2.2]octane dication Salts; Efficient Fluorination Agents and Functionalization Mediators for Organic Compounds. Advances in Organic Synthesis Vol. 2 (2006), Bentham Science, San Francisco 213-267
23. Zupan M., Papez M., and Stavber S. J. Fluorine Chem. 78 (1996) 137-140
24. Zupan M., Iskra J., and Stavber S. J. Fluorine Chem. 70 (1995) 7-8
25. Zupan M., Iskra J., and Stavber S. Bull. Chem. Soc. Jpn. 68 (1995) 1655-1660
26. Zupan M., Iskra J., and Stavber S. Tetrahedron 52 (1996) 11341-11348
27. Stavber S., Jereb M., and Zupan M. Synlett (1999) 1375-1378
28. Stavber S., Jereb M., and Zupan M. J. Phys. Org. Chem. 15 (2002) 56-61
29. Bienvenu A., Barthelemy A., Boichut S., Marquet B., Billard T., and Langlois B.R. Collect. Czech. Chem. Commun. 67 (2002) 1467-1478
30. Grunwald E., and Winstein S. J. Am. Chem. Soc. 70 (1948) 846-854
31. Bentley T.W., Dauschmidt J.P., Llewellyn G., and Mayr H. J. Org. Chem. 57 (1992) 2387-2392
32. Hansch C., Leo A., and Taft R.W. Chem. Rev. 91 (1991) 165-195
33. Nonoyama N., Chiba K., Hisatome K., Suzuki H., and Shintani F. Tetrahedron Lett. 40 (1999) 6933-6937
34. Eberson L., Hartshorn M.P., Radner F., and Persson O. J. Chem. Soc., Perkin Trans. 2 (1998) 59-70
35. Eberson L., Hartshorn M.P., Radner F., and Persson O. J. Chem. Soc., Chem. Commun. (1996) 215-216
36. Banks R.E., Mohialdinkhaffaf S.N., Lal G.S., Sharif I., and Syvret R.G. J. Chem. Soc., Chem. Commun. (1992) 595-596
37. Singh S., Desmarteau D.D., Zuberi S.S., Witz M., and Huang H.N. J. Am. Chem. Soc. 109 (1987) 7194-7196
38. Misaki S. J. Fluorine Chem. 17 (1981) 159-171
39. Stavber S., and Zupan M. J. Org. Chem. 50 (1985) 3609-3612