Synthesis of α-CF3 ketones from alkenes and electrophilic trifluoromethylating reagents by visible-light driven photoredox catalysis

Journal of Fluorine Chemistry

Volumn 167, Issue , 2014, Pages 79-83

  Li, Lun ^a   Chen, Qing Yun ^a   Guo, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Electrophilic; Ketone; Photoredox; Radical; Trifluoromethylation; Visible light

Indexed keywords

EID: 85027918034     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.05.013     Document Type: Article

References (63)

1. C.K. Prier, D.A. Rankic, and D.W.C. MacMillan Chem. Rev. 113 2013 5322 5363
2. A. Studer Angew. Chem. Int. Ed. 51 2012 8950 8958
3. K. Zeitler Angew. Chem. Int. Ed. 48 2009 9785 9789
4. Y.-Q. Zou, J.-R. Chen, and W.-J. Xiao Angew. Chem. Int. Ed. 52 2013 11701 11703
5. F. Teplý Collect. Czech. Chem. Commun. 76 2011 859 917
6. J.M.R. Narayanam, and C.R.J. Stephenson Chem. Soc. Rev. 40 2011 102 113
7. Y. Xi, H. Yi, and A. Lei Org. Biomol. Chem. 11 2013 2387 2403
8. T.P. Yoon ACS Catal. 3 2013 895 902
9. J.W. Tucker, and C.R.J. Stephenson J. Org. Chem. 77 2012 1617 1622
10. T.P. Yoon, M.A. Ischay, and J. Du Nature 2 2010 527 532
11. D.M. Schultz, and T.P. Yoon Science 343 2014 985 993
12. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 Wiley Chichester, UK
13. J.P. Bégué, and D.B. Delphon Bioorganic and Medicinal Chemistry of Fluorine 2008 Wiley Hoboken, NJ
14. K. Uneyama Organofluorine Chemistry 2006 Blackwell Oxford, UK
15. P. Kirsch Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2004 Wiley-VCH Weinheim, Germany
16. R.D. Chambers Fluorine in Organic Chemistry 2004 Blackwell Oxford, UK
17. T. Hiyama Organofluorine Compounds, Chemistry and Applications 2000 Springer New York
18. C.-P. Zhang, Q.-Y. Chen, Y. Guo, J.-C. Xiao, and Y.-C. Gu Chem. Soc. Rev. 41 2012 4536 4559
19. C.-P. Zhang, Q.-Y. Chen, Y. Guo, and J.-C. Xiao Tetrahedron 69 2013 10955 10989
20. C.-P. Zhang, Q.-Y. Chen, Y. Guo, J.-C. Xiao, and Y.-C. Gu Coord. Chem. Rev. 261 2014 28 72
21. N. Iqbal, J. Jung, S. Park, and E.J. Cho Angew. Chem. Int. Ed. 53 2014 539 542
22. H. Jiang, Y. Cheng, Y. Zhang, and S. Yu Eur. J. Org. Chem. 2013 5485 5492
23. P.V. Pham, D.A. Nagib, and D.W.C. MacMillan Angew. Chem. Int. Ed. 50 2011 6119 6122
24. E. Kim, S. Choi, H. Kim, and E.J. Cho Chem. Eur. J. 19 2013 6209 6212
25. Y. Yasu, T. Koike, and M. Akita Angew. Chem. Int. Ed. 51 2012 9567 9571
26. P. Xu, J. Xie, Q. Xue, C. Pan, Y. Cheng, and C. Zhu Chem. Eur. J. 19 2013 14039 14042
27. Y. Yasu, T. Koike, and M. Akita Chem. Commun. 49 2013 2037 2039
28. P. Xu, A. Abdukader, K. Hu, Y. Cheng, and C. Zhu Chem. Commun. 50 2014 2308 2310
29. D.J. Wilger, N.J. Gesmundo, and D.A. Nicewicz Chem. Sci. 4 2013 3160 3165
30. J.D. Nguyen, J.W. Tucker, M.D. Konieczynska, and C.R.J. Stephenson J. Am. Chem. Soc. 133 2011 4160 4163
31. C.J. Wallentin, J.D. Nguyen, P. Finkbeiner, and C.R.J. Stephenson J. Am. Chem. Soc. 134 2012 8875 8884
32. Y. Ye, and M.S. Sanford J. Am. Chem. Soc. 134 2012 9034 9037
33. D.A. Nagib, M.E. Scott, and D.W.C. MacMillan J. Am. Chem. Soc. 131 2009 10875 10877
34. N. Iqbal, S. Choi, E. Kim, and E.J. Cho J. Org. Chem. 77 2012 11383 11387
35. D.A. Nagib, and D.W.C. MacMillan Nature 480 2011 224 228
36. Y. Yasu, Y. Arai, R. Tomita, T. Koike, and M. Akita Org. Lett. 16 2014 780 783
37. D. Cantillo, O. de Frutos, J.A. Rincón, C. Mateos, and C.O. Kappe Org. Lett. 16 2014 896 899
38. S.H. Oh, Y.R. Malpani, N. Ha, Y.S. Jung, and S.B. Han Org. Lett. 16 2014 1310 1313
39. A. Carboni, G. Dagousset, E. Magnier, and G. Masson Org. Lett. 16 2014 1240 1243
40. Y. Yasu, T. Koike, and M. Akita Org. Lett. 15 2013 2136 2139
41. J. Xie, X. Yuan, A. Abdukader, C. Zhu, and J. Ma Org. Lett. 16 2014 1768 1771
42. 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
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. N. Kamigata, K. Udodaira, and T. Shimizu Phosphorus Sulphur Silicon 129 1997 155 168
45. K. Sato, T. Yuki, R. Yamaguchi, T. Hamano, A. Tarui, M. Omote, I. Kumadaki, and A. Ando J. Org. Chem. 74 2009 3815 3819
46. P. Novák, A. Lishchynskyi, and V.V. Grushin J. Am. Chem. Soc. 134 2012 16167 16170
47. Z. He, R. Zhang, M. Hu, L. Li, C. Ni, and J. Hu Chem. Sci. 4 2013 3478 3483
48. T. Umemoto, and S. Ishihara J. Am. Chem. Soc. 115 1993 2156 2164
49. T. Umemoto, and K. Adachi J. Org. Chem. 59 1994 5692 5699
50. J.-A. Ma, and D. Cahard J. Org. Chem. 68 2003 8726 8729
51. A.E. Allen, and D.W.C. MacMillan J. Am. Chem. Soc. 132 2010 4986 4987
52. K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto Tetrahedron Lett. 131 1990 6391 6394
53. B.R. Langlois, E. Laurent, and N. Roidot Tetrahedron Lett. 33 1992 1291 1294
54. Y. Itoh, and K. Mikami Org. Lett. 7 2005 4883 4885
55. Y. Itoh, and K. Mikami Org. Lett. 7 2005 649 651
56. Y. Itoh, and K. Mikami J. Fluorine Chem. 127 2006 539 544
57. Y. Itoh, and K. Mikami Tetrahedron 62 2006 7199 7203
58. K. Mikami, Y. Tomita, Y. Ichikawa, K. Amikura, and Y. Itoh Org. Lett. 8 2006 4671 4673
59. C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, and J.-C. Xiao Chem. Commun. 47 2011 6632 6634
60. A. Deb, S. Manna, A. Modak, T. Patra, S. Maity, and D. Maiti Angew. Chem. Int. Ed. 52 2013 9747 9750
61. Y.-F. Wang, G.H. Lonca, and S. Chiba Angew. Chem. Int. Ed. 53 2014 1067 1071 and Ref. [3c] and Ref. 3b
62. S. Lin, M.A. Ischay, C.G. Fry, and T.P. Yoon J. Am. Chem. Soc. 133 2011 19350 19353
63. M.A. Ischay, Z.T. Lu, and P. Yoon J. Am. Chem. Soc. 132 2010 8572 8574