From carboxylic acids to the trifluoromethyl group using BrF3

Tetrahedron

Volumn 66, Issue 20, 2010, Pages 3579-3582

  Cohen, Or ^a   Mishani, Eyal ^b   Rozen, Shlomo ^a  

^a TEL AVIV UNIVERSITY   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; AROMATIC COMPOUND; BENZOIC ACID; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER; FLUORIDE; FLUOROFORM; METHYL GROUP; ORGANIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 77950858792     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.045     Document Type: Article

References (38)

1. Prakash G.K.S., Krishnamurti R., and Olah G.A. J. Am. Chem. Soc. 111 (1989) 393
2. Langlois B.R., and Billard T. Synth. (2003) 185
3. Ait-Mohand S., Takechi N., Medebielle M., and Dolbier Jr. W.R. Org. Lett. 26 (2001) 4271
4. Shono T., Kise N., and Oka H. Tetrahedron Lett. 32 (1991) 6567
5. Umemoto T., and Ishihara S. J. Fluorine Chem. 92 (1998) 181
6. Wang C.-L. J. Org. React. 34 (1985) 319
7. For earlier works with BrF3 see:. Michalak R.S., Wilson S.R., and Martin J.C. J. Am. Chem. Soc. 106 (1984) 7529
8. Soelch R.R., Mauer G.W., and Lemal D.M. J. Org. Chem. 50 (1985) 5845
9. Rozen S., and Lerman O. J. Org. Chem. 58 (1993) 239
10. Rozen S., Mishani E., and Bar-Haim A. J. Org. Chem. 59 (1994) 2918
11. Cohen O., and Rozen S. Tetrahedron 64 (2008) 5362
12. Hagooly Y., Cohen O., and Rozen S. Tetrahedron Lett. 50 (2009) 392
13. Ben-David I., Rechavi D., Mishani E., and Rozen S. J. Fluorine Chem. 97 (1999) 75
14. Rozen S., and Ben-David I. J. Fluorine Chem. 76 (1996) 145
15. Cohen O., Sasson R., and Rozen S. J. Fluorine Chem. 127 (2006) 433
16. Sasson R., Hagooly A., and Rozen S. Org. Lett. 5 (2003) 769
17. Rozen S. Acc. Chem. Res. 38 (2005) 803
18. Sasson R., Hagooly A., and Rozen S. Org. Lett. 5 (2003) 769
19. 3 group with one carbon less than the starting material:. Sasson R., and Rozen S. Tetrahedron 60 (2005) 1083
20. Kuroboshi M., and Hiyama T. Chem. Lett. 5 (1992) 827
21. Savarin C., Srogl J., and Liebeskind S.L. Org. Lett. 2 (2000) 3229
22. This material is commercially available.
23. For a preliminary communication see:. Rozen S., and Mishani E. J. Chem. Soc., Chem. Commun. (1994) 2081
24. Rozen S., Rechavi D., and Hagooly A. J. Fluorine Chem. 111 (2001) 161
25. Rozov L.A., Huang C.G., Halpern D.F., Vernice G.G., and Ramig K. Tetrahedron: Asymmetry 8 (1997) 3023
26. Wolniewicz A., and Dmowski W. J. Fluorine Chem. 109 (2001) 95
27. Boguslavskaya L.S., Kartashov A.V., and Chuvatkin N.N. Zh. Org. Khim. (Eng. Transln.) 25 (1989) 1835
28. Duddeck H., Spitzer M., and Bolte G. Liebigs Ann. Chem. 3 (1985) 545
29. Rozen S., and Gal C. J. Org. Chem. 52 (1987) 4928
30. Mlinaric-Majerski K., Veljkovic J., Kaselj M., and Marchand A.P. Eur. J. Org. Chem. (2004) 2923
31. Alexandrov A.M., Sorochinskii A.E., and Krasnoshchek A.P. Zh. Org. Khim. (Eng. Transln.) 15 (1979) 336
32. Levesque G., Gressier J.C., and Proust M. Synth. (1981) 963
33. Sasson R., Hagooly A., and Rozen S. J. Fluorine Chem. 127 (2006) 962
34. Dagan S., and Amirav A. J. Am. Mass. Spectrom. 6 (1995) 120
35. Amirav A., Gordin A., and Tzanani N. Rapid Commun. Mass Spectrom. 15 (2001) 811
36. Alon T., and Amirav A. Rapid Commun. Mass Spectrom. 20 (2006) 2579
37. Amirav A., Gordin A., Poliak M., and Fialkov A.B. J. Mass. Spectrom. 43 (2008) 141
38. Lehmann E., Naumann D., and Schmeisser M. Z. Anorg. Allg. Chem. 388 (1972) 1