Development and challenges in the copper-catalyzed trifluoromethylation of alkenes

Synlett

Volumn 24, Issue 15, 2013, Pages 1882-1886

  Liu, Xiaowu ^a   Wu, Xiaoxing ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

Author keywords

allylic alcohol; copper catalyzed; migration; radical; trifluoromethylation

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; ALPHA,ALPHA DIARYL ALLYLIC ALCOHOL DERIVATIVE; COPPER; FLUORINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; METHYLATION; OXIDATION; TRIFLUOROMETHYLATION;

EID: 84881643464     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1339684     Document Type: Article

References (77)

1. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
2. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
3. Yamazaki, T.; Taguchi, T.; Ojima, I. In Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; Wiley-Blackwell: Chichester, 2009, 3.
4. Umemoto, T. Chem. Rev. 1996, 96, 1757.
5. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
6. Shimizu M. Hiyama, T. Angew. Chem. Int. Ed. 2005 44
7. Schlosser, M. Angew. Chem. Int. Ed. 2006, 45, 5432.
8. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1.
9. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
10. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature (London) 2011, 473, 470.
11. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem. Int. Ed. 2012, 51, 5048.
12. Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 6679.
13. Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617.
14. Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975.
15. Prakash, G. K. S.; Chacko, S. Curr. Opin. Drug Discovery Dev. 2008, 11, 793. For recent selected examples, see:
16. Miyake, Y.; Ota, S.-i.; Shibata, M.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7809.
17. Novák, P.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2012, 134, 16167.
18. Hu, M.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2012, 134, 15257.
19. Zhao, T. S. N.; Szabó , K. J. Org. Lett. 2012, 14, 3966.
20. Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N. Org. Lett. 2012, 14, 3596.
21. Xu, J.; Xiao, B.; Xie, C.-Q.; Luo, D.-F.; Liu, L.; Fu, Y. Angew. Chem. Int. Ed. 2012, 51, 12551.
22. Miyake, Y.; Ota, S.-i.; Nishibayashi, Y. Chem. Eur. J. 2012, 18, 13255.
23. Prakash, G. K. S.; Jog, P. V.; Batamack, P. T. D.; Olah, G. A. Science 2012, 338, 1324.
24. Herrmann, A. T.; Smith, L. L.; Zakarian, A. J. Am. Chem. Soc. 2012, 134, 6976.
25. Liu, C.-B.; Meng, W.; Li, F.; Wang, S.; Nie, J.; Ma, J.-A. Angew. Chem. Int. Ed. 2012, 51, 6227.
26. Deng, Q.- H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769.
27. Mu, X.; Wu, T.; Wang, H.-Y.; Guo, Y.-L.; Liu, G. J. Am. Chem. Soc. 2012, 134, 878.
28. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875.
29. Parsons, A. T.; Buchwald, S. L. Angew. Chem. Int. Ed. 2011, 50, 9120.
30. Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300.
31. Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410.
32. Eisenberger, P.; Gischig, S.; Togni, A. Chem. Eur. J. 2006, 12, 2579.
33. Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem. Int. Ed. 2007, 46, 754.
34. Umemoto, T.; Ishihara, S. Tetrahedron Lett. 1990, 31, 3579.
35. Umemoto, T.; Ishihara, S. J. Am. Chem. Soc. 1993, 115, 2156.
36. Chu, L.; Qing, F.-L. Org. Lett. 2012, 14, 2106.
37. Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. J. Org. Chem. 2012, 77, 11383.
38. Matsubara, S.; Mitani, M.; Utimoto, K. Tetrahedron Lett. 1987, 28, 5857.
39. Kobayashi, Y.; Yamamoto, K.; Kumadaki, I. Tetrahedron Lett. 1979, 20, 4071.
40. Su, D.- B.; Duan, J.-X.; Chen, Q.-Y. Tetrahedron Lett. 1991, 32, 7689.
41. Kim, J.; Shreeve, J. M. Org. Biomol. Chem. 2004, 2, 2728.
42. Konno, T.; Takehana, T.; Mishima, M.; Ishihara, T. J. Org. Chem. 2006, 71, 3545.
43. Parsons, A. T.; Senecal, T. D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2012, 51, 2947.
44. Shimizu, R.; Egami, H.; Hamashima, Y.; Sodeoka, M. Angew. Chem. Int. Ed. 2012, 51, 4577.
45. Mizuta, S.; Galicia-López, O.; Engle, K. M.; Verhoog, S.; Wheelhouse, K.; Rassias, G.; Gouverneur, V. Chem. Eur. J. 2012, 18, 8583.
46. Mizuta, S.; Engle, K. M.; Verhoog, S.; Galicia-López, O.; ODuill, M.; Médebielle, M.; Wheelhouse, K.; Rassias, G.; Thompson, A. L.; Gouverneur, V. Org. Lett. 2013, 15, 1250.
47. Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458.
48. Wang, X.; Ye, Y.; Ji, G.; Zhang, S.; Feng, J.; Zhang, Y.; Wang, J. Org. Lett. 2013, 15, 3730.
49. Yasu, Y.; Koike, T.; Akita, M. Angew. Chem. Int. Ed. 2012, 51, 9567.
50. Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462.
51. Janson, P. G.; Ghoneim, I.; IIchenko, N. O.; Szabó , K. J. Org. Lett. 2012, 14, 2882.
52. Egami, H.; Shimizu, R.; Sodeoka, M. Tetrahedron Lett. 2012, 53, 5503.
53. Li Y.: Studer A. Angew. Chem. Int. Ed., 2012. 51, 8221
54. Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Chem. Commun. 2011, 47, 6632.
55. Kim, E.; Choi, S.; Kim, H.; Cho, E. J. Chem. Eur. J. 2013, 19, 6209. Carbotrifluoromethylation:
56. Egami, H.; Shimizu, R.; Kawamura, S.; Sodeoka, M. Angew. Chem. Int. Ed. 2013, 52, 4000.
57. Egami, H.; Shimizu, R.; Sodeoka, M. J. Fluorine Chem. 2013, 152, 51. Hydrotrifluoromethylation:
58. Mizuta, S.; Verhoog, S.; Engle, K. M.; Khotavivattana, T.; ODuill, M.; Wheelhouse, K.; Rassias, G.; Médebielle, M.; Gouverneur, V. J. Am. Chem. Soc. 2013, 135, 2505.
59. Wu, X.; Chu, L.; Qing, F.-L. Angew. Chem. Int. Ed. 2013, 52, 2198.
60. Wilger, D. J.; Gesmundo, N. J.; Nicewicz, D. A. Chem. Sci. 2013, 4, 3160. Aminotrifluoromethylation:
61. Yasu, Y.; Koike, T.; Akita, M. Org. Lett. 2013, 15, 2136.
62. Egami, H.; Kawamura, S.; Miyazaki, A.; Sodeoka, M. Angew. Chem. Int. Ed. 2013, 52, 7841.
63. Lu, D.-F.; Zhu, C.-L.; Xu, H. Chem. Sci. 2013, 4, 2478.
64. Christoph, R.; Roland, H. Chem. Ber. 1965, 98, 2471.
65. Aureliano Antunes, C. S.; Bietti, M.; Ercolani, G.; Lanzalunga, O.; Salamone, M. J. Org. Chem. 2005, 70, 3884. For a review on radical aryl migration:
66. Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649.
67. Li, L.; Cai, P.; Guo, Q.; Xue, S. J. Org. Chem. 2008, 73, 3516.
68. Shinde, A. B.; Shrigadi, N. B.; Bhat, R. P.; Samant, S. D. Synth. Commun. 2004, 34, 309.
69. Liu, X.; Xiong, F.; Huang, X.; Xu, L.; Li, P.; Wu, X. Angew. Chem. Int. Ed. 2013, 52, 6962.
70. Sevenard, D. V.; Sosnovskikh, V. Y.; Kolomeitsev, A. A.; Königsmann, M. H.; Röschenthaler, G.-V. Tetrahedron Lett. 2003, 44, 7623.
71. Sosnovskikh, V. Y.; Usachev, B. I.; Sevenard, D. V.; Röschenthaler, G.-V. J. Org. Chem. 2003, 68, 7747.
72. Wang, C.-L.; Li, H.-Q.; Meng, W.-D.; Qing, F.-L. Bioorg. Med. Chem. Lett. 2005, 15, 4456.
73. Sato, K.; Omote, M.; Ando, A.; Kumadaki, I. Org. Lett. 2004, 6, 4359.
74. Lubczyk, V.; Bachmann, H.; Gust, R. J. Med. Chem. 2002, 45, 5358.
75. Ciganek, E. J. Org. Chem. 1995, 60, 4439.
76. Egami, H.; Shimizu, R.; Usui, Y.; Sodeoka, M. Chem. Commun. 2013, 49, 7346.
77. Chen, Z.-M.; Bai, W.; Wang, S.-H.; Yang, B.-M.; Tu, Y.-Q.; Zhang, F.-M. Angew. Chem. Int. Ed. 2013, in press DOI: 10.1002/anie.201304557.