Solvent-free fluorination of organic compounds using N-F reagents

Tetrahedron Letters

Volumn 48, Issue 15, 2007, Pages 2671-2673

  Stavber, Gaj ^a   Zupan, Marko ^a,b   Stavber, Stojan ^b  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

Accufluor NFSi; Fluorination; Selectfluor F TEDA BF4; Solvent free

Indexed keywords

CARBONYL DERIVATIVE; FLUORINE; NITROGEN; ORGANIC COMPOUND; REAGENT; SOLVENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; FLUORINATION; PHYSICAL CHEMISTRY;

EID: 33947135385     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.077     Document Type: Article

References (33)

1. In: Baasner B., Hagemann H., and Tatlow J.C. (Eds). Organo-Fluorine Compounds Houben-Weyl Methods of Organic Chemistry Vol. E10a-c (1999), Georg Thieme, Stuttgart, New York
2. Chambers R.D. Fluorine in Organic Chemistry (2004), Blackwell, Oxford
3. In: Banks R.E., Smart B.E., and Tatlow J.C. (Eds). Organofluorine Chemistry. Principles and Commercial Applications (1996), Plenum Press, New York, London
4. In: Laali K.K., and Atta-Ur-Rahman (Eds). Advances in Organic Synthesis Modern Organofluorine Chemistry-Synthetic Aspects Vol. 2 (2006), Bentham Science, Amsterdam
5. Merrit R.F., and Johnson F.A. J. Org. Chem. 31 (1966) 1859-1863
6. Purrington S.T., Kagen B.S., and Patrick T.B. Chem. Rev. 86 (1986) 997-1018
7. Rozen S. Acc. Chem. Rev. 21 (1988) 307-312
8. Chambers R.D., Parsons M., Sandford G., Thomas E., Trmcic J., and Moilliet J.S. Tetrahedron 62 (2006) 7162-7167 and references cited therein
9. Chambers R.D., Skinner C.J., Thomson J., and Hutchinson J.C.S. Chem. Commun. 17 (1995)
10. Chambers R.D., Holling D., Sanford G., Batsanov A.S., and Howard J.A.K. J. Fluorine Chem. 125 (2004) 661-671 and references cited therein
11. Chambers R.D., and Spink R.C.H. Chem. Commun. (1999) 883-884
12. Chambers R.D., Fox M.A., and Sanford G. Lab Chip 5 (2005) 1132-1139 and references cited therein
13. Rozen S. Chem. Rev. 96 (1996) 1717-1736
14. Zupan M. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Functional Groups, supplement D2, The Chemistry of Halides, Pseudo-Halides and Azides (1995), Wiley, Chichester 821-860
15. 2b, 61-157.
16. Lal G.S., Pez G.P., and Syvret R.G. Chem. Rev. 96 (1996) 1737-1755
17. Taylor D.S., Kotoris C.C., and Hum G. Tetrahedron 55 (1999) 12431-12477
18. 2b, pp 159-181 and references cited therein.
19. Singh R.P., and Schreeve J.M. Chem. Res. 37 (2004) 31-34
20. 2b, pp 213-268 and references cited therein.
21. Anastas P.T., and Warner J.C. Green Chemistry: Theory and Practice (1998), Oxford University Press, New York
22. Stavber G., Zupan M., Jereb M., and Stavber S. Org. Lett. 6 (2004) 4973-4976
23. In: Tanaka K. (Ed). Solvent-free Organic Synthesis (2003), Wiley, Weinheim
24. Tanaka K., and Toda F. Chem. Rev. 100 (2000) 1025-1074
25. Prakash G.K.S., Mathew T., Hoole D., Esteves P.M., Wang Q., Rasul G., and Olah G.A. J. Am. Chem. Soc. 126 (2004) 15770-15776 and references cited therein
26. Pravst I., Zupan M., and Stavber S. Green Chem. 8 (2006) 1001-1005 and references cited therein
27. Marque S., Snoussi H., Loupy A., Plé N., and Turck A. J. Fluorine Chem. 125 (2004) 1847-1851
28. Barbier P., Mohr P., Muller M., and Masciadri R. J. Org. Chem. 63 (2002) 6984-6989
29. Hasegava M., Ishii H., and Fuchigami T. Tetrahedron Lett. 43 (2002) 1503-1505
30. Differding E., and Ofner H. Synlett (1991) 187-189
31. 13 did not considerably improve the formation of the 2,2-difluoro product, while fluorination of mono fluoro compound 5 with an equimolar amount of the N-F reagent afforded no more than 15% of the difluoro product.
32. Zupan M., Iskra J., and Stavber S. Bull. Chem. Soc. Jpn. 68 (1995) 1655-1660
33. A gram scale experiment was performed in the case of fluorination of compound 8 with 1c and no uncontrollable exotherm was observed.