The first Cu(I)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilane in ionic liquids

Organic and Biomolecular Chemistry

Volumn 2, Issue 19, 2004, Pages 2728-2734

  Kim, Jinwi ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AROMATIC COMPOUNDS; CATALYSTS; CHROMATOGRAPHY; DRUG PRODUCTS; HEATING; NUCLEAR MAGNETIC RESONANCE; SALTS; SOLVENTS; WATER;

CARBONYL FUNCTIONALITIES; FLUORINATION; IONIC LIQUIDS; ORGANIC HALIDES;

FLUORINE;

EID: 6344223002     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412480b     Document Type: Article

References (48)

1. For recent reviews, see: (a) R. P. Singh and J. M. Shreeve, Ace. Chem. Res., 2004, 37, 31-44;
2. (b) R. P. Singh and J. M. Shreeve, Tetrahedron, 2000, 56, 7613-7632;
3. (c) G. K. S. Prakash and A. K. Yudin, Chem. Rev., 1997, 97, 757-786.
4. (a) J. T. Welch, Tetrahedron, 1987, 43, 3123;
5. (b) Biomedical Aspects of Fluorine Chemistry, ed. R. Filler and Y. Kobayashi, Kodansha Ltd. & Elsevier Biochemical, Tokyo and Amsterdam, 1982;
6. (c) M. Hudlický and A. Pavlath, Chemistry of Organic Fluorine Compounds II: A Critical Review, ACS Monograph 187, American Chemical Society, Washington DC, 1995;
7. (d) Organofluorine Chemistry: Principles and Commercial Application, ed. R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum, New York, 1994, ch. 3;
8. (e) Biomedical; Frontiers of Fluorine Chemistry, ed. I. Ojima, J. R. McCarthy and J. T. Welch, ACS Symposium Series 639, American Chemical Society, Washington DC, 1996.
9. Organofluorine Chemicals and Their Industrial Applications, ed. R. E. Banks, Ellis Harwood Ltd., Chichester, 1979.
10. (a) D. D, DesMarteau, Z. Wu and M. Witz, J. Org. Chem., 1992, 57, 1124-1131;
11. (b) N. R. PatelandR. L. Kirchmeier, Inorg. Chem., 1992, 31, 2537;
12. (c) I. Ruppert, K. Schlich and W. Volbach, Tetrahedron Lett., 1984, 25, 2195;
13. (d) F. L. Taw, B. L. Scott and J. L. Kiplinger, J. Am. Chem. Soc., 2003, 125, 14712;
14. (e) W. B. Farnham, in Synthetic Fluorine Chemistry, ed. G. A. Olah, R. D. Chambers and G. K. S. Prakash, John Wiley & Sons: New York, 1992, ch. 11, and references therein.
15. R. P. Singh, G. Cao, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873-2876.
16. R. P. Singh, R. L. Kirchmeier and J. M. Shreeve, Org. Lett., 1999, 1, 1047-1049.
17. R. P. Singh, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2579-2581.
18. R. P. Singh and J. M. Shreeve, J. Org. Chem., 2000, 65, 3241-3243.
19. R. P. Singh and J. M. Shreeve, J. Org. Chem., 2001, 66, 1436-1440.
20. J. Wiedemann, T. Heiner, G. Mloston, G. K. S. Prakash and G. A. Olah, Angew. Chem., Int. Ed., 1998, 37, 820-821.
21. (a) Y Kobayashi and I. Kumadaki, Tetrahedron Lett., 1969, 47, 4095;
22. Y. Kobayashi, K. Yamamoto, T. Asai, M. Nakano and I. Kumadaki, J. Chem. Soc., 1980, 2755-2671;
23. (c) N. V. Kondratenko, E. P. Vechirko and L. M. Yagupolskii, Synthesis, 1980, 932-933.
24. H. Urata and T. Fuchikami, Tetrahedron Lett., 1991, 32, 91-94.
25. (a) D. W. Kim, C. E. Song and D. Y. Chi, J. Am. Chem. Soc., 2002, 124, 10278-10279;
26. (b) D. W. Kim, C. E. Song and D. Y. Chi, J. Org. Chem., 2003, 68, 4281-4285;
27. (c) D. W. Kim and D. Y. Chi, Angew. Chem., Int. Ed., 2004, 43, 483-485.
28. (a) K. K. Laali and G. I. Borodkin, J. Chem. Soc., Perkin Trans. 2, 2002, 953-957;
29. (b) C. B. Murray, G. Sandford and S. R. Korn, J. Fluorine Chem., 2003, 123, 81-84.
30. (a) C. Baudequin, J.-F. Loubassou, J.-C. Plaquevent and D. J. Cahard, J. Fluorine Chem., 2003, 122, 189-193;
31. (b) Y. Hamashima, H. Takano, D. Hotta and M. Sodeoka, Org. Lett., 2003, 5, 3225-3228;
32. (c) T. Kitazume and G. Tanaka, J. Fluorine Chem., 2000, 106, 211-215.
33. (a) R. P. Singh, S. Manandhar and J. M. Shreeve, Tetrahedron Lett., 2002, 43, 9497-9499;
34. (b) R. P. Singh, S. Manandhar and J. M. Shreeve, Synthesis, 2003, 1579-1585;
35. (c) R. R Singh and J. M. Shreeve, Chem. Commun., 2003, 1366-1367;
36. (d) R. P. Singh, R. W. Winter, G. L. Gard, Y. Gao and J. M. Shreeve, Inorg. Chem., 2003, 42, 6142-6146;
37. (e) Y. R. Mirzaei and J. M. Shreeve, Synthesis, 2003, 24-26.
38. Y. R. Mirzaei, H. Xue and J. M. Shreeve, Inorg. Chem., 2004, 43, 361-367.
39. B. A. Omotowa and J. M. Shreeve, Organometallics, 2004, 23, 783-791.
40. J. Kim, R. P. Singh and J. M. Shreeve, Inorg. Chem., 2004, 43, 2960-2966.
41. Y. Gao and J. M. Shreeve, Synthesis, 2004, 7, 1072-1082.
42. M. Van der Puy, J. Fluorine Chem., 1997, 81, 187-191.
43. (a) Q. Chen and J. Duan, Tetrahedron Lett., 1993, 34(26), 4241-4244;
44. (b) Y. Kobayashi, K. Yamamoto and I. Kumadaki, Tetrahedron Lett., 1979, 42, 4071-4073.
45. V. Ya. Sosnovskikh, D. V. Sevenard, B. I. Usachev and G.-V. Röschenthaler, Tetrahedron Lett. 2003, 2097-2099.
46. D. M. Sevenard, V. Ya. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann and G.-V. Röschenthaler, Tetrahedron Lett., 2003, 7623-7627.
47. N. Kimizuka and T. Nakashima, Langmuir, 2001, 17, 6759-6761.
48. P. Bonhôte, A. P. Dias, N. Papageorgiou, K. Kalyanasundaram and M. Grätzel, Inorg. Chem., 1996, 35, 1168-1178.