Trifluoromethylation of organic compounds and related reactions

Synthesis

Volumn , Issue 11, 2010, Pages 1865-1882

  Sato, Kazuyuki ^a   Tarui, Atsushi ^a   Omote, Masaaki ^a   Ando, Akira ^a   Kumadaki, Itsumaro ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

Diethylzinc; Perfluoroalkyl iodide unsaturated ketones; Perfluoroalkylation; Rhodium complexes; Silyl enol ethers; Trifluoromethyl iodide; Trifluoromethylation

Indexed keywords

DIETHYLZINC; PERFLUOROALKYLATION; RHODIUM COMPLEXES; SILYL ENOL ETHERS; TRIFLUOROMETHYL; TRIFLUOROMETHYLATION; UNSATURATED KETONES;

ADDITION REACTIONS; CARBONYLATION; CARBOXYLIC ACIDS; COMPLEXATION; COPPER; COPPER POWDER; COPPER POWDER METALLURGY; ETHERS; FLUORINE; FLUORINE COMPOUNDS; KETONES; ORGANIC ACIDS; RHODIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

RHODIUM COMPOUNDS;

(ETHOXYCARBONYL)DIFLUOROMETHYL DERIVATIVE; ALIPHATIC COMPOUND; ALKENYL GROUP; AROMATIC COMPOUND; CARBOXYLIC ACID DERIVATIVE; CHEMICAL COMPOUND; COPPER; DIETHYLZINC; DIFLUOROMETHYLENE DERIVATIVE; ETHYLBROMODIFLUOROACETIC ACID; FLUORINE; FLUORINE DERIVATIVE; HALIDE; KETONE DERIVATIVE; METHYL IODIDE; ORGANIC COMPOUND; RHODIUM COMPLEX; TRIFLUOROMETHYL DERIVATIVE; TRIFLUOROMETHYL IODIDE; UNCLASSIFIED DRUG;

ALPHA CHAIN; BETA SHEET; CATALYSIS; DRUG BINDING SITE; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; METHYLATION; MICHAEL ADDITION; REVIEW; TRIFLUOROMETHYLATION;

EID: 77952786362     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218745     Document Type: Review

References (43)

1. Smart B E., Chem. Rev. 1996 96 1555
2. Resnati G, Soloshonok V A., Tetrahedron 1996 52 1
3. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications Filler R Kobayashi Y Yagupolskii L M. Elsevier Amsterdam 1993
4. Welch J T., Tetrahedron 1987 43 3123
5. Kobayashi Y, Kumadaki I, Tetrahedron Lett. 1969 10 4095
6. Kobayashi Y, Kumadaki I, Sato S, Hara N, Chikami E, Chem. Pharm. Bull. 1970 18 2334
7. Kobayashi Y, Yamamoto K, Kumadaki I, Tetrahedron Lett. 1979 20 4071
8. Kobayashi Y, Yamamoto K, Asai T, Nakano M, Kumadaki I, J. Chem. Soc., Perkin Trans. 1 1980 2755
9. Sato K, Kawata R, Ama F, Omote M, Ando A, Kumadaki I, Chem. Pharm. Bull. 1999 47 1013
10. Sato K, Tamura M, Tamoto K, Omote M, Ando A, Kumadaki I, Chem. Pharm. Bull. 2000 48 1023
11. Sato K, Tarui A, Kita T, Ishida Y, Tamura H, Omote M, Ando A, Kumadaki I, Tetrahedron Lett. 2004 45 5735
12. Sato K, Omote M, Ando A, Kumadaki I, Org. Synth. 2006 83 177
13. Sato K, Omote M, Ando A, Kumadaki I, Org. Lett. 2004 6 4359
14. Sato K, Ishida Y, Murata E, Oida Y, Mori Y, Okawa M, Iwase K, Tarui A, Omote M, Kumadaki I, Ando A, Tetrahedron 2007 63 12735
15. Sato K, Higashinagata M, Yuki T, Tarui A, Omote M, Kumadaki I, Ando A, J. Fluorine Chem. 2008 129 51
16. Sato K, Yuki T, Yamaguchi R, Hamano T, Tarui A, Omote M, Kumadaki I, Ando A, J. Org. Chem. 2009 74 3815
17. Sato K, Yamazoe S, Akashi Y, Hamano T, Miyamoto A, Sugiyama S, Tarui A, Omote M, Kumadaki I, Ando A, J. Fluorine Chem. 2010 131 86
18. Kobayashi Y, Kumadaki I, Ohsawa A, Yamada T, Chem. Pharm. Bull. 1972 20 1839
19. Kobayashi Y, Kumadaki I, Yamamoto K, J. Chem. Soc., Chem. Commun. 1977 536
20. Burton D J., Wiemers D M., J. Am. Chem. Soc. 1985 107 5014
21. Kitagawa O, Miura A, Kobayashi Y, Taguchi T, Chem. Lett. 1990 1011
22. Sato K, Nakazato S, Enko H, Tsujita H, Fujita K, Yamamoto T, Omote M, Ando A, Kumadaki I, [nl] J. Fluorine Chem. 2003 121 105
23. For example, Honda reported the rhodium-catalyzed Michael reaction of unfluorinated ethyl bromoacetate:, Honda T, Wakabayashi H, Kanai K, Chem. Pharm. Bull. 2002 50 307
24. Kanai K, Wakabayashi H, Honda T, Org. Lett. 2000 2 2549
25. Metal-catalyzed 1,4-addition of carbonyl compound was reported:, Fagnou K, Lautens M, Chem. Rev. 2003 103 169
26. Hayashi T, Synlett 2001 879
27. Prakash G S. K., Krishnamurti R, Olah G A., J. Am. Chem. Soc. 1989 111 393
28. Wang Z, Lu X, Tetrahedron 1995 51 2639
29. Tsuji J, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis John Wiley & Sons Chichester 2002
30. Transition Metals for Organic Synthesis Beller M Bolm C VCH Weinheim 1998
31. Ma J.-A, Cahard D, J. Org. Chem. 2003 68 8726
32. Umemoto T, Adachi K, J. Org. Chem. 1994 59 5692
33. Crusiani G, Margaretha P, J. Fluorine Chem. 1987 37 95
34. Kitazume T, Ishikawa N, J. Am. Chem. Soc. 1985 107 5186
35. Sato K, Yuki T, Tarui A, Omote M, Kumadaki I, Ando A, Tetrahedron Lett. 2008 49 3558
36. Itoh Y, Mikami K, Org. Lett. 2005 7 649
37. Itoh Y, Mikami K, Org. Lett. 2005 7 4883
38. Itoh Y, Mikami K, Tetrahedron 2006 62 7199
39. Mikami K, Tomita Y, Ichikawa Y, Amikura K, Itoh Y, Org. Lett. 2006 8 4671
40. Itoh Y, Houk K N., Mikami K, J. Org. Chem. 2006 71 8918
41. Chen Q.-Y, Yang Z.-Y, Zhao C.-X, Qiu Z.-M, J. Chem. Soc., Perkin Trans. 1 1988 563
42. Tarui A, Ozaki D, Nakajima N, Yokota Y, Sokeirik Y S., Sato K, Omote M, Kumadaki I, Ando A, Tetrahedron Lett. 2008 49 3839; and references therein
43. Sato K, Yamazoe S, Yamamoto R, Ohata S, Tarui A, Omote M, Kumadaki I, Ando A, Org. Lett. 2008 10 2405