Dialkylzinc-aceelerated α-trifluoromethylation of carbonyl compounds catalyzed by late-transition-metal complexes

Chemistry Letters

Volumn 37, Issue 10, 2008, Pages 1080-1081

  Tomita, Yuichi ^a   Itoh, Yoshimitsu ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67650497391     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2008.1080     Document Type: Article

References (48)

1. a) V. A. Soloshonok, K. Mikami, T. Yamazaki, J. T. Welch, J. F. Honek, Current Fluoroorganic Chemistry, ACS Symposium Series #949, 2006.
2. b) K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, 2006.
3. c) M. Shimizu, T. Hiyama, Angew. Chem., Int. Ed. 2005, 44, 214.
4. d) J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119.
5. e) K. Mikami, Y. Itoh, M. Yamanaka, Chem. Rev. 2004, 104, 1.
6. f) T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa, M. Shimizu, Organofluorine Compounds, Springer-Verlag, Berlin Heidelberg, 2000.
7. g) Organofluorine Chemistry, ed. by R. D. Chambers, Springer, Berlin, 1997.
8. h) K. Iseki. Tetrahedron 1998, 54, 13887.
9. Perfluoroalkylation of silyl and germyl enol ethers of esters and ketones: K. Miura, Y. Takeyama, K. Oshima, K. Utimoto, Bull. Chem. Soc. Jpn. 1991, 64, 1542, perfluoroalkylation of ketone silyl enol ethers provided the products in good yields except for trifluoromethylation. Trifluoromethylation of ketone germyl enol ethers takes long time to give good yield.
10. a) J. E. Huheey, J. Phys. Chem. 1965, 69, 3284.
11. b) M. Yoshida, N. Kamigata, J. Fluorine Chem. 1990, 49, 1.
12. a) Y. Itoh, K. Mikami, Org. Lett. 2005, 7, 649.
13. b) Y. Itoh, K. Mikami, J. Fluorine Chem. 2006, 127, 539.
14. c) Y. Itoh, K. Mikami, Org. Lett. 2005, 7, 4883.
15. d) Y. Itoh, K. Mikami, Tetrahedron 2006, 62, 7199.
16. e) Y. Itoh, K. N. Houk, K. Mikami, J. Org. Chem. 2006, 71, 8918.
17. f) K. Mikami, Y. Tomita, Y. Ichikawa, K. Amikura, Y. Itoh, Org. Lett. 2006, 8, 4671.
18. g) Y. Tomita, Y. Ichikawa, Y. Itoh, K. Kawada, K. Mikami, Tetrahedron Lett. 2007, 48, 8922.
19. a) J. Åhman, J. P. Wolfe, M. V. Troutman, M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 1918.
20. b) S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402.
21. T. Hama, D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 4976.
22. X. Liu, I. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 5182.
23. T. Hama, X. Liu, D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 11176.
24. Y. Tomita, Y. Itoh, K. Mikami, 86th Annual Meeting of the Chemical Society of Japan, Funabashi, March 27-30, 2006, Abstr., No. 1J2-16, on July 25, 1997, we obtained the α-trifluoromethyl ketone (2a) in 56% yield via the late-transition-metal catalysis.
25. Review: a) B.-T. Grobel, D. Seebach, Synthesis 1977, 357.
26. b) D. Seebach, Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
27. c) G. Wittig, P. Davis, G. Koenig, Chem. Ber. 1951, 84, 627.
28. K. Sato, T. Yuki, A. Tami, M. Omote, I. Kumadaki, A. Ando, Tetrahedron Lett. 2008, 49, 3558.
29. 3I to late-transition-metal complex: a) R. P. Hughes, Adv. Organomet. Chem. 1990, 31, 183.
30. b) J. A. Morrison, Adv. Organomet. Chem. 1993, 35, 211.
31. 3I to Ir complexes: a) P. J. Albietz, Jr., B. P. Cleary, W. Paw, R. Eisenberg, J. Am. Chem. Soc. 2001, 123, 12091.
32. b) P. J. Albietz, Jr., B. P. Cleary, W. Paw, R. Eisenberg, Inorg. Chem. 2002, 41, 2095.
33. c) T. R. Greene, W. R. Roper, J. Organomet. Chem. 1986, 299, 245.
34. d) R. B. King, A. Efraty, J. Organomet. Chem. 1971, 27, 409.
35. e) S. A. Gardner, M. D. Rausch, Inorg. Chem. 1974, 13, 997.
36. 3 carbonyl compounds: a) M. Schlosser, in Organometallics in Synthesis-A Manual, ed. by M. Schlosser, John Wiley & Sons, Chichester, 1994, pp. 1-166.
37. b) E. F. Murphy, R. Murugavel, H. W. Roesky, Chem. Rev. 1997, 97, 3425.
38. c) H. Plenio, Chem. Rev. 1997, 97, 3363, and references cited therein.
39. I9FNMR using BTF (10 μL, 0.082 mmol) as an internal standard.
40. Silyl enol ether of α-methyl cyclohexanone consists of thermodynamic and kinetic enol ethers (87:13).
41. Reviews on the construction of quaternary carbons: a) S. F. Martin, Tetrahedron 1980, 36, 419.
42. b) K. Fuji, Chem. Rev. 1993, 93, 2037.
43. c) E. J. Corey, A. Guzman-Perez, Angew. Chem., Int. Ed. 1998, 37, 388.
44. d) J. Christoffers, A. Mann, Angew. Chem., Int. Ed. 2001, 40, 4591.
45. e) I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105.
46. f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363.
47. g) B. M. Trost, C. Jiang, Synthesis 2006, 369.
48. 15 For radical trifluoromethylation of ester silyl enol ether, see ref. 2.