Recent progress in transition-metal-catalyzed trifluoromethylation of olefins using electrophilic CF3 reagents

Journal of Fluorine Chemistry

Volumn 167, Issue , 2014, Pages 30-36

  Koike, Takashi ^a   Akita, Munetaka ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkene difunctionlalization; Electrophilic CF3 reagent; Photocatalysis; Step economy; Transition metal catalyst; Trifluoromethylation

Indexed keywords

EID: 85027953033     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.06.025     Document Type: Article

References (92)

1. T. Hiyama Organofluorine Compounds: Chemistry and Applications 2000 Springer Berlin
2. Special issue on Fluorine in the life science ChemBioChem 5 2004 570 722
3. K. Müller, C. Faeh, and F. Diederich Science 317 2007 1881 1886
4. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 Wiley-Blackwell Chichester
5. J.-A. Ma, and D. Cahard Chem. Rev. 104 2004 6119 6146
6. M. Shimizu, and T. Hiyama Angew. Chem. Int. Ed. 44 2005 214 231
7. J.-A. Ma, and D. Cahard J. Fluorine Chem. 128 2007 975 996
8. N. Shibata, S. Mizuta, and T. Toru J. Synth. Org. Chem. Jpn. 66 2008 215 228
9. J.-A. Ma, and D. Cahard Chem. Rev. 108 2008 PR1 PR43
10. I. Katsuyama J. Synth. Org. Chem. Jpn. 67 2009 992 1000
11. J. Hu, W. Zhang, and F. Wang Chem. Commun. 2009 7465 7478
12. H. Amii J. Synth. Org. Chem. Jpn. 69 2011 752 762
13. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475 4521
14. T. Furuya, A.S. Kamlet, and T. Ritter Nature 473 2011 470 477
15. T. Besset, C. Schneider, and D. Cahard Angew. Chem. Int. Ed. 51 2012 5048 5050
16. A. Studer Angew. Chem. Int. Ed. 51 2012 8950 8958
17. C. Hollingworth, and V. Gouverneur Chem. Commun. 48 2012 2929 2942
18. H. Liu, Z. Gu, and X. Jiang Adv. Synth. Catal. 355 2013 617 626
19. T. Liang, C.N. Neumann, and T. Ritter Angew. Chem. Int. Ed. 52 2013 8214 8264
20. Y. Macé, and E. Magnier Eur. J. Org. Chem. 2012 2479 2494
21. N. Shibata, A. Matsnev, and D. Cahard Beistein J. Org. Chem. 2010 10.3762/bjoc.6.65
22. T. Umemoto, and S. Ishihara Tetrahedron Lett. 31 1990 3579 3582
23. T. Umemoto, and S. Ishihara J. Am. Chem. Soc. 115 1993 2156 2164
24. T. Umemoto Chem. Rev. 96 1996 1757 1777
25. P. Eisenberger, S. Gischig, and A. Togni Chem. Eur. J. 12 2006 2579 2586
26. I. Kieltsch, P. Eisenberger, and A. Togni Angew. Chem. Int. Ed. 46 2007 754 757
27. J. Xu, X. Liu, and Y. Fu Tetrahedron Lett. 55 2014 585 594
28. E. Merino, and C. Nevado Chem. Soc. Rev. 2014 10.1039/c4cs00025k
29. T.P. Yoon, and M.A. Ischay J. Du, Nat. Chem. 2 2010 527 532
30. J.M.R. Narayanam, and C.R.J. Stephenson Chem. Soc. Rev. 40 2011 102 113
31. J. Xuan, and W.-J. Xiao Angew. Chem. Int. Ed. 51 2012 6828 6838
32. D.P. Hari, and B. König Angew. Chem. Int. Ed. 52 2013 4734 4743
33. C.K. Prier, D.A. Rankic, and D.W.C. MacMillan Chem. Rev. 113 2013 5322 5363
34. D.M. Schultz, and T.P. Yoon Science 2014 10.1126/science.1239176
35. M.N. Hopkinson, B. Sahoo, J.-L. Li, and F. Glorius Chem. Eur. J. 20 2014 3874 3886
36. T. Koike, and M. Akita Top. Catal. 57 2014 967 974
37. A.T. Parsons, and S.L. Buchwald Angew. Chem. Int. Ed. 50 2011 9120 9123
38. J. Xu, Y. Fu, D.-F. Luo, Y.-Y. Jiang, B. Xiao, Z.-J. Liu, T.-J. Gong, and L. Liu J. Am. Chem. Soc. 133 2011 15300 15303
39. X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, and J. Wang J. Am. Chem. Soc. 133 2011 16410 16413
40. L. Chu, and F.-L. Qing Org. Lett. 14 2012 2106 2109
41. R. Shimizu, H. Egami, Y. Hamashima, and M. Sodeoka Angew. Chem. Int. Ed. 51 2012 4577 4580
42. S. Mizuta, O. Galicia-López, K.M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias, and V. Gouverneur Chem. Eur. J. 18 2012 8583 8587
43. S. Mizuta, K.M. Engle, S. Verhoog, O. Galicia-López, M. O'Duill, M. Médebielle, K. Wheelhouse, G. Rassias, A.L. Thompson, and V. Gouverneur Org. Lett. 15 2013 1250 1253
44. K. M͡niz Chem. Soc. Rev. 33 2004 166 174
45. J.P. Wolfe Synlett 2008 2913 2947
46. K.H. Jensen, and M.S. Sigman Org. Biomol. Chem. 6 2008 4083 4088
47. F. Cardona, and A. Goti Nat. Chem. 1 2009 269 275
48. R.I. McDonald, G. Liu, and S.S. Stahl Chem. Rev. 111 2011 2981 3019
49. J.P. Wolfe Angew. Chem. Int. Ed. 51 2012 10224 10225
50. N. Kamigata, T. Fukushima, and M. Yoshida J. Chem. Soc., Chem. Commun. 1989 1559 1560
51. N. Kamigata, T. Fukushima, Y. Terakawa, M. Yoshida, and H. Sawada J. Chem. Soc. Perkin Trans. I 1991 627 633
52. J. Ignatowska, and W. Dmowski J. Fluorine Chem. 128 2007 997 1006
53. J.D. Nguyen, J.W. Tucker, M.D. Konieczynska, and C.R.J. Stephenson J. Am. Chem. Soc. 133 2011 4160 4163
54. C.-J. Wallentin, J.D. Nguyen, P. Finkbeiner, and C.R.J. Stephenson J. Am. Chem. Soc. 134 2012 8875 8884
55. S.H. Oh, Y.R. Malpani, N. Ha, Y.-S. Jung, and S.B. Han Org. Lett. 16 2014 1310 1313
56. P.G. Janson, I. Ghoneim, N.O. Ilchenko, and K.J. Szabó Org. Lett. 14 2012 2882 2885
57. R. Zhu, and S.L. Buchwald J. Am. Chem. Soc. 134 2012 12462 12465
58. Y. Yasu, T. Koike, and M. Akita Angew. Chem. Int. Ed. 51 2012 9567 9571
59. H. Egami, R. Shimizu, and M. Sodeoka Tetrahedron Lett. 53 2012 5503 5506
60. Y.-T. He, L.-H. Li, Y.-F. Yang, Y.-Q. Wang, J.-Y. Luo, X.-Y. Liu, and Y.-M. Liang Chem. Commun. 49 2013 5687 5689
61. R. Zhu, and S.L. Buchwald Angew. Chem. Int. Ed. 52 2013 12655 12658
62. Y. Yasu, Y. Arai, R. Tomita, T. Koike, and M. Akita Org. Lett. 16 2014 780 783
63. Y. Li, and A. Studer Angew. Chem. Int. Ed. 51 2012 8221 8224
64. T. Fuchikami, Y. Shibata, and H. Urata Chem. Lett. 1987 521 524
65. E. Kim, S. Choi, H. Kim, and E.J. Cho Chem. Eur. J. 19 2013 6209 6212
66. X.-Y. Jiang, and F.-L. Qing Angew. Chem. Int. Ed. 52 2013 14177 14180
67. C. Feng, and T.-P. Loh Chem. Sci. 3 2012 3458 3462
68. D.-F. Lu, C.-L. Zhu, and H. Xu Chem. Sci. 4 2013 2478 2482
69. Q. Yu, and S. Ma Chem. Eur. J. 19 2013 13304 13308
70. A. Carboni, G. Dagousset, E. Magnier, and G. Masson Org. Lett. 16 2014 1240 1243
71. Y. Yasu, T. Koike, and M. Akita Org. Lett. 15 2013 2136 2139
72. H. Egami, S. Kawamura, A. Miyazaki, and M. Sodeoka Angew. Chem. Int. Ed. 52 2013 7841 7844
73. J.-S. Lin, Y.-P. Xiong, C.-L. Ma, L.-J. Zhao, B. Tan, and X.-Y. Liu Chem. Eur. J. 20 2014 1332 1340
74. F. Wang, X. Qi, Z. Liang, P. Chen, and G. Liu Angew. Chem. Int. Ed. 53 2014 1881 1886
75. H. Egami, R. Shimizu, S. Kawamura, and M. Sodeoka Angew. Chem. Int. Ed. 52 2013 4000 4003
76. X. Dong, R. Sang, Q. Wang, X.-Y. Tang, and M. Shi Chem. Eur. J. 19 2013 16910 16915
77. H. Egami, R. Shimizu, and M. Sodeoka J. Fluorine Chem. 152 2013 51 55
78. P. Xu, J. Xie, Q. Xue, C. Pan, Y. Cheng, and C. Zhu Chem. Eur. J. 19 2013 14039 14042
79. W. Kong, M. Casimiro, E. Merino, and C. Nevado J. Am. Chem. Soc. 135 2013 14480 14483
80. H. Egami, R. Shimizu, Y. Usui, and M. Sodeoka Chem. Commun. 49 2013 7346 7348
81. Z.-M. Chen, W. Bai, S.-H. Wang, B.-M. Yang, Y.-Q. Tu, and F.-M. Zhang Angew. Chem. Int. Ed. 52 2013 9781 9785
82. X. Mu, T. Wu, H.-y. Wang, Y.-l. Guo, and G. Liu J. Am. Chem. Soc. 134 2012 878 881
83. W. Kong, M. Casimiro, N. Fuentes, E. Merino, and C. Nevado Angew. Chem. Int. Ed. 52 2013 13086 13090
84. L. Shi, X. Yang, Y. Wang, H. Yang, and H. Fu Adv. Synth. Catal. 356 2014 1021 1028
85. Q. Lu, C. Liu, P. Peng, Z. Liu, L. Fu, J. Huang, and A. Lei Asian J. Org. Chem. 3 2014 273 276
86. F. Yang, P. Klumphu, Y.-M. Liang, and B.H. Lipshutz Chem. Commun. 50 2014 936 938
87. L. Li, M. Deng, S.-C. Zheng, Y.-P. Xiong, B. Tan, and X.-Y. Liu Org. Lett. 16 2014 504 507
88. Y.-T. He, L.-H. Li, Y.-F. Yang, Z.-Z. Zhou, H.-L. Hua, X.-Y. Liu, and Y.-M. Liang Org. Lett. 16 2014 270 273
89. N.O. Ilchenko, P.G. Janson, and K.J. Szabó J. Org. Chem. 78 2013 11087 11091
90. S. Mizuta, S. Verhoog, K.M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Médebielle, and V. Gouverneur J. Am. Chem. Soc. 135 2013 2505 2508
91. X. Wu, L. Chu, and F.-L. Qing Angew. Chem. Int. Ed. 52 2013 2198 2202
92. D.J. Wilger, N.J. Gesmundo, and D.A. Nicewicz Chem. Sci. 4 2013 3160 3165