Visible-light-mediated trifluoroethylation of 2-isocyanobiaryl with trifluoroethyl iodide: Synthesis of 6-trifluoroethyl-phenanthridines

Journal of Fluorine Chemistry

Volumn 168, Issue , 2014, Pages 50-54

  Fu, Weijun ^a   Zhu, Mei ^a   Xu, Chen ^a   Zou, Guanglong ^b   Wang, Zhiqiang ^a   Ji, Baoming ^a  

^a LUOYANG NORMAL UNIVERSITY   (China)

^b GUIZHOU MINZU UNIVERSITY   (China)

Author keywords

Isocyanobiaryl; Phenanthridines; Photoredox; Radical reactions; Trifluoroethylation

Indexed keywords

EID: 84918585460     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.08.022     Document Type: Article

References (53)

1. P. Kirsch Modern Fluoroorganic Chemistry 2004 Wiley-VCH Weinheim
2. K. Müller, C. Faeh, and F. Diederich Science 317 2007 1881 1886
3. W.K. Hagmann J. Med. Chem. 51 2008 4359 4369
4. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
5. M. Shimizu, and T. Hiyama Angew. Chem. Int. Ed. 44 2005 214 231
6. K. Uneyama J. Fluorine Chem. 129 2008 550 576
7. T. Yamazaki, T. Taguchi, and I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 Wiley-Blackwell Chichester
8. G.G. Dubinina, H. Furutachi, and D.A. Vicic J. Am. Chem. Soc. 130 2008 8600 8601
9. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475 4521
10. X.F. Wu, H. Neumann, and M. Beller Chem. - Asian J. 7 2012 1744 1754
11. A. Studer Angew. Chem. Int. Ed. 51 2012 8950 8958
12. H. Liu, Z. Gu, and X. Jiang Adv. Synth. Catal. 355 2013 617 626
13. R.J. Lundgren, and M. Stradiotto Angew. Chem. Int. Ed. 49 2010 9322 9324
14. S. Roy, B.T. Gregg, G.W. Gribble, and V.-D. Le Tetrahedron 67 2011 2161 2195
15. T. Besset, C. Chneider, and D. Cahard Angew. Chem. Int. Ed. 51 2012 5048 5050
16. T. Koike, and M. Akita Top. Catal. 57 2014 967 974
17. V.C.R. McLoughlin, and J. Thrower Tetrahedron 25 1969 5921 5940
18. S. Xu, H.-H. Chen, J.-J. Dai, and H.-J. Xu Org. Lett. 16 2014 2306 2309
19. Y.-C. Zhao, and J.-B. Hu Angew. Chem. Int. Ed. 51 2012 1033 1036
20. A.-P. Liang, X.-J. Li, D.-F. Liu, J.-Y. Li, D.-P. Zou, Y.-J. Wu, and Y.-S. Wu Chem. Commun. 48 2012 8273 8275
21. Y.-S. Feng, C.-Q. Xie, W.-L. Qiao, and H.-J. Xu Org. Lett. 15 2013 936 939
22. J. Hwang, K. Park, J. Choe, H. Min, K.H. Song, and S. Lee J. Org. Chem. 79 2014 3267 3271
23. Y. Fujiwara, J.A. Dixon, F. O'Hara, E.D. Funder, D.D. Dixon, R.A. Rodriguez, R.D. Baxter, B. Herle, N. Sach, M.R. Collins, Y. Ishihara, and P.S. Baran Nature 492 2012 95 100
24. C.K. Prier, D.A. Rankic, and D.W.C. MacMillan Chem. Rev. 113 2013 5322 5363
25. K. Zeitler Angew. Chem. Int. Ed. 48 2009 9785 9789
26. J. Xuan, and W.-J. Xiao Angew. Chem. Int. Ed. 51 2012 6828 6838
27. F. Teplý Collect. Czech. Chem. Commun. 76 2011 859 917
28. D. Ravelli, and M. Fagnoni ChemCatChem 4 2012 169 171
29. J.W. Tucker, and C.R.J. Stephenson J. Org. Chem. 77 2012 1617 1622
30. J.M.R. Narayanam, and C.R.J. Stephenson Chem. Soc. Rev. 40 2011 102 113
31. T.P. Yoon ACS Catal. 3 2013 895 902
32. N. Iqbal, S. Choi, E. Kim, and E.J. Cho J. Org. Chem. 77 2012 11383 11387
33. Y. Yasu, T. Koike, and M. Akita Chem. Commun. 49 2013 2037 2039
34. D.J. Wilger, N.J. Gesmundoa, and D.A. Nicewicz Chem. Sci. 4 2013 3160 3165
35. D.A. Nagib, and D.W.C. MacMillan Nature 480 2011 224 228
36. N. Iqbal, S. Choi, E. Ko, and E.J. Cho Tetrahedron Lett. 53 2012 2005 2008
37. Y. Ye, and M.S. Sanford J. Am. Chem. Soc. 134 2012 9034 9037
38. L.M. Kreis, S. Krautwald, N. Pfeiffer, R.E. Martin, and E.M. Carreira Org. Lett. 15 2013 1634 1637
39. W. Fu, F. Xu, Y. Fu, C. Xu, S. Li, and D. Zou Eur. J. Org. Chem. 2014 709 712
40. M. Zhu, W. Fu, G. Zou, C. Xu, and Z. Wang J. Fluorine Chem. 163 2014 23 27
41. W. Fu, M. Zhu, F. Xu, Y. Fu, C. Xu, and D. Zou RSC Adv. 4 2014 17226 17229
42. M. Zhu, Z. Wang, F. Xu, J. Yu, and W. Fu J. Fluorine Chem. 156 2013 21 25
43. W. Fu, F. Xu, Y. Fu, M. Zhu, J. Yu, C. Xu, and D. Zou J. Org. Chem. 78 2013 12202 12206
44. M. Tobisu, K. Koh, T. Furukawa, and N. Chatani Angew. Chem. Int. Ed. 51 2012 11363 11366
45. B. Zhang, C. Mück-Lichtenfeld, C.G. Daniliuc, and A. Studer Angew. Chem. Int. Ed. 52 2013 10792 10795
46. Q. Wang, X. Dong, T. Xiao, and L. Zhou Org. Lett. 15 2013 4846 4849
47. Y. Cheng, H. Jiang, Y. Zhang, and S. Yu Org. Lett. 15 2013 5520 5523
48. X. Sun, and S. Yu Org. Lett. 16 2014 2938 2941
49. D. Leifert, C.G. Daniliuc, and A. Studer Org. Lett. 15 2013 6286 6289
50. B. Zhang, C.G. Daniliuc, and A. Studer Org. Lett. 16 2014 250 253
51. H. Jiang, Y. Cheng, R. Wang, M. Zheng, Y. Zhang, and S. Yu Angew. Chem. Int. Ed. 52 2013 13289 13292
52. J. Liu, C. Fan, H. Yin, C. Qin, G. Zhang, X. Zhang, H. Yi, and A. Lei Chem. Commun. 50 2014 2145 2147
53. T. Xiao, L. Li, G. Lin, Q. Wang, P. Zhang, Z. Mao, and L. Zhou Green Chem. 16 2014 2418 2421