Radical trifluoromethylation of Ti ate enolate: possible intervention of transformation of Ti(IV) to Ti(III) for radical termination

Journal of Fluorine Chemistry

Volumn 127, Issue 4-5 SPEC. ISS., 2006, Pages 539-544

  Itoh, Yoshimitsu ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

CF3 ketone; Radical addition; Ti ate enolate; Trifluoromethylation

Indexed keywords

EID: 33646420100     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.03.011     Document Type: Article

References (42)

1. Ma J.-A., and Cahard D. Chem. Rev. 104 (2004) 6119-6146
2. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1-16
3. Hiyama T., Kanie K., Kusumoto T., Morizawa Y., and Shimizu M. Organofluorine Compounds (2000), Springer-Verlag, Berlin Heidelberg
4. In: Soloshonok V.A. (Ed). Enantiocontrolled Synthesis of Fluoro-Organic Compounds (1999), Wiley, Chichester
5. In: Ramachandran P.V. (Ed). Asymmetric Fluoroorganic Chemistry, Synthesis, Applications, and Future Directions (2000), American Chemical Society
6. In: Chambers R.D. (Ed). Organofluorine Chemistry (1997), Springer, Berlin
7. Iseki K. Tetrahedron 54 (1998) 13887-13914
8. In: Ojima I., McCarthy J.R., and Welch J.T. (Eds). Biomedical Frontiers of Fluorine Chemistry (1996), American Chemical Society, Washington DC
9. B. E. Smart (Ed.), Chem. Rev. 96 (1996) 1555-1824 (Thematic issue of fluorine chemistry).
10. In: Banks R.E., Smart B.E., and Tatlow J.C. (Eds). Organofluorine Chemistry: Principles and Commercial Applications (1994), Plenum Press, New York
11. McClinton M.A., and McClinton D.A. Tetrahedron 48 (1992) 6555-6666
12. Hudlicky M. Chemistry of Organic Fluorine Compounds. 2nd ed. (1976), Ellis Horwood, Chichester
13. Itoh Y., Yamanaka M., and Mikami K. Org. Lett. 5 (2003) 4803-4806. Our preliminary report on the radical trifluoromethylation of Ti ate enolates
14. Itoh Y., Yamanaka M., and Mikami K. Org. Lett. 5 (2003) 4807-4809. Our preliminary report on the radical trifluoromethylation of Ti ate enolates
15. Itoh Y., Yamanaka M., and Mikami K. J. Am. Chem. Soc. 126 (2004) 13174-13175. Our preliminary report on the radical trifluoromethylation of Ti ate enolates
16. Itoh Y., and Mikami K. Org. Lett. 7 (2005) 649-651. Our preliminary report on the radical trifluoromethylation of Ti ate enolates
17. Itoh Y., and Mikami K. Org. Lett. 7 (2005) 4883-4885. Our preliminary report on the radical trifluoromethylation of Ti ate enolates
18. Iseki K., Nagai T., and Kobayashi Y. Tetrahedron Lett. 34 (1993) 2169-2170. Trifluoromethylation of Li enolate of hindered imides (only exception for the use of Li enolate). They have succeeded in trifluoromethylation by adopting Evans oxazolidinones with bulky substitutent at α position to suppress defluorination
19. Iseki K., Nagai T., and Kobayashi Y. Tetrahedron: Asymmetry 5 (1994) 961-974. Trifluoromethylation of Li enolate of hindered imides (only exception for the use of Li enolate). They have succeeded in trifluoromethylation by adopting Evans oxazolidinones with bulky substitutent at α position to suppress defluorination
20. Miura K., Taniguchi M., Nozaki K., Oshima K., and Utimoto K. Tetrahedron Lett. 31 (1990) 6391-6394. Perfluoroalkylation of silyl and germyl enol ethers of esters and ketones. Perfluoroalkylation of silyl enol ethers provided the products in good yields except for trifluoromethylation. Trifluoromethylation of ketone germyl enol ethers proceeds in good yield
21. Miura K., Takeyama Y., Oshima K., and Utimoto K. Bull. Chem. Soc. Jpn. 64 (1991) 1542-1553. Perfluoroalkylation of silyl and germyl enol ethers of esters and ketones. Perfluoroalkylation of silyl enol ethers provided the products in good yields except for trifluoromethylation. Trifluoromethylation of ketone germyl enol ethers proceeds in good yield
22. Cantacuzène D., Wakselman C., and Dorme R. J. Chem. Soc. Perkin Trans. 1 (1977) 1365-1371. Trifluoromethylation of enamines
23. Kitazume T., and Ishikawa N. J. Am. Chem. Soc. 107 (1985) 5186-5191. Trifluoromethylation of enamines
24. Langlois B.R., Laurent E., and Roidot N. Tetrahedron Lett. 33 (1992) 1291-1294. Trifluoromethylation of enol acetates
25. Yagupol L.M., skii N.V., Kondratenko G.N., and Timofeeva. J. Org. Chem. USSR 20 (1984) 115-118. There are some reports of trifluoromethylation using CF3+
26. Umemoto T., and Ishihara S. J. Am. Chem. Soc. 115 (1993) 2156-2164. There are some reports of trifluoromethylation using CF3+
27. Umemoto T., and Adachi K. J. Org. Chem. 59 (1994) 5692-5699. There are some reports of trifluoromethylation using CF3+
28. Schlosser M. In: Schlosser M. (Ed). Organometallics in Synthesis - A Manual (1994), John Wiley & Sons, Chichester 1-166. M-F interaction plays an important role in defluorination of α-CF3 carbonyl compounds
29. Murphy E.F., Murugavel R., and Roesky H.W. Chem. Rev. 97 (1997) 3425-3468. M-F interaction plays an important role in defluorination of α-CF3 carbonyl compounds
30. Plenio H. Chem. Rev. 97 (1997) 3363-3384. M-F interaction plays an important role in defluorination of α-CF3 carbonyl compounds
31. Nozaki K., Oshima K., and Utimoto K. J. Am. Chem. Soc. 109 (1987) 2547-2549
32. Stork G., and Hudrlik P.F. J. Am. Chem. Soc. 90 (1968) 4462-4464
33. Stork G., and Hudrlik P.F. J. Am. Chem. Soc. 90 (1968) 4464-4465
34. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian, Inc Wallingford CT (2004). Geometry optimization was done using Gaussian 03 program package. Gaussian 03, Revision C.02
35. Becke A.D. Phys. Rev. A38 (1988) 3098-3100. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level
36. Becke A.D. J. Chem. Phys. 98 (1993) 1372-1377. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level
37. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level
38. Lee C., Yang W., and Parr R.G. Phys Rev. B37 (1988) 785-788. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level
39. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 270-283. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level
40. Wadt W.R., and Hay P.J. J. Chem. Phys. 82 (1985) 284-298. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level
41. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 299-310. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level
42. Hehre W.J., Radom L., von Ragué Schleyer P., and Pople J.A. Ab initio Molecular Orbital Theory (1986), Wiley, New York and references cited therein. The structure of the Ti(IV) ketyl radical intermediate was optimized at UB3LYP/631+LAN (LANL2DZ for Ti, 6-31+G* for others) level