Copper-mediated trifluoromethylation of propiolic acids: Facile synthesis of α-trifluoromethyl ketones

Chemical Science

Volumn 4, Issue 9, 2013, Pages 3478-3483

  He, Zhengbiao ^a   Zhang, Rui ^a   Hu, Mingyou ^a   Li, Lingchun ^a   Ni, Chuanfa ^a   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FACILE SYNTHESIS; FLUOROALKYLATION; NEW PROTOCOL; PROPIOLIC ACID; TRIFLUOROMETHYLATION; TRIFLUOROMETHYLKETONE;

KETONES;

COPPER;

EID: 84886821536     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc51613j     Document Type: Article

References (52)

1. M. Shimizu, T. Hiyama: Angew. Chem., Int. Ed. 2005 44: 214
2. K. Müller, C. Faeh, F. Diederich: Science 2007 317: 1881
3. W. K. Hagmann: J. Med. Chem. 2008 51: 4359-4369
4. K. L. Kirk: Org. Process Res. Dev. 2008 12: 305-321
5. Fluorine in Medicinal Chemistry and Chemical Biology, ed. I. Ojima, Wiley, Chichester, 2009
6. J.-P. Bégué and D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley-VCH, Weinheim, 2008
7. Organofluorine Compounds: Chemistry and Application, ed. T. Hiyama, Springer, Berlin, 2000, pp. 183-234
8. Organofluorine Chemistry: Principles and Commercial Applications, ed. R. E. Banks, B. E. Smart and C. J. Tatlow, Springer, New York, 1994, pp. 237-262
9. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur: Chem. Soc. Rev. 2008 37: 320
10. Organofluorine Compounds in Medicinal Chemistry & Biomedical Applications, ed. R. Filler, Y. Kobayashi and L. M. Yagupolskii, Elserbier, Amsterdam, 1993
11. M. Schlosser: Angew. Chem., Int. Ed. 2006 45: 5432
12. J.-A. Ma, D. Cahard: J. Fluorine Chem. 2007 128: 975
13. J.-A. Ma, D. Cahard: Chem. Rev. 2008 108: PR1
14. G. K. S. Prakash, S. Chacko: Curr. Opin. Drug Discovery Dev. 2008 11: 793
15. O. A. Tomashenko, V. V. Grushin: Chem. Rev. 2011 111: 4475
16. T. Besset, C. Schneider, D. Cahard: Angew. Chem., Int. Ed. 2012 51: 5048
17. Z. Jin, G. B. Hammond, B. Xu: Aldrichimica Acta 2012 45: 67
18. A. B. Ash, M. P. L. Montagne and A. Markovac, US 3,940,404, 1976
19. G. Alvernhe, B. Langlois, A. Laurent, I. Le Drean, A. Selmi, M. Weissenfels: Tetrahedron Lett. 1991 32: 643
20. N. A. Petasis and M. Myslinska, US Patent Appl. 20090247766
21. P. F. Wang, N. Li, W. M. Liu, S. T. Lee and C. S. Lee, US Patent Appl. 20090102356
22. I. C. Mukhejee, S. H. Ko, J. P. Stables, M. K. Patel, M. L. Brown: Bioorg. Med. Chem. 2004 12: 979
23. G. Q. Shi, X. H. Huang, F. Hong: J. Chem. Soc., Perkin Trans. 1 1996 763
24. K. Sato, M. Higashinagata, T. Yuki, A. Tarui, M. Omote, I. Kumadaki, A. Ando: J. Fluorine Chem. 2008 129: 51
25. H. Rudler, A. Parlier, C. Denneval, P. Herson: J. Fluorine Chem. 2010 131: 738
26. V. M. Muzalevskiy, V. G. Nenajdenko, A. Y. Rulev, I. A. Ushakov, G. V. Romanenko, A. V. Shastin, E. S. Balenkova, G. Haufe: Tetrahedron 2009 65: 6991
27. R. A. Cox, E. Grant, T. Whitaker, T. Tidwell: Can. J. Chem. 1990 68: 1876
28. N. Yoneda, S. Matsuoka, N. Miyaura, T. Fukuhara, A. Suzuki: Bull. Chem. Soc. Jpn. 1990 63: 2124
29. N. Kamigata, K. Udodaira, T. Shimizu: Phosphorus, Sulfur Silicon Relat. Elem. 1997 129: 155
30. T. Umemoto, S. Ishihara: J. Am. Chem. Soc. 1993 115: 2156
31. T. Umemoto, K. Adachi: J. Org. Chem. 1994 59: 5692
32. A. Togni: Chimia 2008 62: 261
33. A. E. Allen, D. W. C. MacMillan: J. Am. Chem. Soc. 2010 132: 4986
34. Y. Itoh, K. Mikami: Org. Lett. 2005 7: 4883
35. Y. Itoh, K. Mikami: Tetrahedron 2006 62: 7199
36. K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, K. Utimoto: Tetrahedron Lett. 1990 31: 6391
37. P. V. Pham, D. A. Nagib, D. W. C. MacMillan: Angew. Chem., Int. Ed. 2011 50: 6119
38. D. A. Nagib, M. E. Scott, D. W. C. MacMillan: J. Am. Chem. Soc. 2009 131: 10875
39. K. Sato, T. Yuki, R. Yamaguchi, T. Hamano, A. Tarui, M. Omote, I. Kumadaki, A. Ando: J. Org. Chem. 2009 74: 3815
40. K. Sato, A. Tarui, M. Omote, A. Ando, I. Kumadaki: Synthesis 2010 1865
41. B. Morandi, E. K. Carreira: Angew. Chem., Int. Ed. 2011 50: 9085
42. P. Novak, A. Lishchynskyi, V. V. Grushin: J. Am. Chem. Soc. 2012 134: 16167
43. C. P. Zhang, Z. L. Wang, Q. Y. Chen, C. T. Zhang, Y. C. Gu, J. C. Xiao: Chem. Commun. 2011 47: 6632
44. M. Hu, C. Ni, J. Hu: J. Am. Chem. Soc. 2012 134: 15257
45. Z. He, T. Luo, M. Hu, Y. Cao, J. Hu: Angew. Chem., Int. Ed. 2012 51: 3944
46. Z. He, M. Hu, T. Luo, L. Li: Angew. Chem., Int. Ed. 2012 51: 11545
47. R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, A. Togni: Angew. Chem., Int. Ed. 2009 48: 4332
48. A. E. Allen, D. W. C. MacMillan: J. Am. Chem. Soc. 2010 132: 4986
49. K. Niedermann, N. Frueh, E. Vinogradova, M. S. Wiehn, A. Moreno, A. Togni: Angew. Chem., Int. Ed. 2011 50: 1059
50. R. Koller, Q. Huchet, P. Battaglia, J. M. Welch, A. Togni: Chem. Commun. 2009 5993
51. S. Fantasia, J. M. Welch, A. Togni: J. Org. Chem. 2010 75: 1779
52. B. Greedy, V. Gouverneur: Chem. Commun. 2001 233