Nucleophilic trifluoromethylation using trifluoromethyl iodide. A new and simple alternative for the trifluoromethylation of aldehydes and ketones

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4271-4273

  Aït Mohand, Samia ^a   Takechi, Naoto ^a   Médebielle, Maurice ^b   Dolbier Jr , William R ^a  

^a University of Florida ^*  (United States)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001548395     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016933x     Document Type: Article

References (19)

1. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555-6666.
2. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786.
3. Singh, R. P.; Shreeve, J. M. Tetrahedron 2000, 56, 7613-7632.
4. Large, S.; Roques, N.; Langlois, B. R. J. Org. Chem. 2000, 65, 8848-8856.
5. Billard, T.; Langlois, B. R.; Blond, G. Eur. J. Org. Chem. 2001, 1467-1471.
6. Kitazume, T.; Ishikawa, N. J. Am. Chem. Soc. 1985, 107, 5186-5191.
7. 3Br, see: Francese, C.; Tordeux, M.; Wakselman, C. J. Chem. Soc., Chem. Commun. 1987, 642-643.
8. Burkholder, C. R.; Dolbier, W. R., Jr.; Médebielle, M. J. Org. Chem. 1998, 63, 5385-5394.
9. Burkholder, C. R.; Dolbier, W. R., Jr.; Médebielle, M. J. Fluorine Chem. 2001, 109, 39-48.
10. Pawelke, G. J. Fluorine Chem. 1991, 52, 229.
11. Petrov, V. A. Tetrahedron Lett. 2001, 42, 3267-3289.
12. A temperature of -20 °C was chosen for the photoinduced process in order to minimize the extent of thermal decomposition of the charge-transfer complex, which occurs at room temperature.
13. 2/hexane = 8:2) to give 1-phenyl-2,2,2-trifluoroethanol in a yield of 78%.
14. Krishnamurthy, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984-989.
15. Matsuda, T.; Harada, T.; Nakajima, N.; Itoh, T.; Nakamura, K. J. Org. Chem. 2000, 65, 157-163.
16. Tordeux, M.; Francese, C.; Wakselman, C. J. Chem. Soc., Perkin Trans. 1 1987, 1951-1957.
17. Pirkle, W. H.; Hoekstra, M. S. J. Org. Chem. 1974, 39, 3904-3906.
18. Dolbier, W. R., Jr.; Burkholder, C. R.; Piedrahita, C. A. J. Fluorine Chem. 1982, 20, 637-647.
19. 13C NMR δ 157.1. 131.7, 129.9, 127.4, 127.0, 124.2 (q, J = 275 Hz), 121.2, 121.2, 120.7, 110.9, 72.1 (q J = 32 Hz).