Citation: He Jiangqi, Lou Shaojie, Xu Danqian. Recent Advances in Transition-Metal Catalyzed C—H Bond Fluorination[J]. Chinese Journal of Organic Chemistry, ;2016, 36(6): 1218-1228. doi: 10.6023/cjoc201512040 shu

Recent Advances in Transition-Metal Catalyzed C—H Bond Fluorination

1.
Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Xu Danqian, chrc@zjut.edu.cn
Received Date: 26 December 2015
Revised Date: 25 January 2016

Fund Project: the China Postdoctoral Science Foundation No.2014M560494Project supported by the National Natural Science Foundation of China No.21361130021

Figures(17)

Organofluorine compounds are widely found in pharmaceuticals, agrochemicals, and materials due to their special properties. However, development of transformations to incorporate fluorine atom is usually a great challenge, because of its highly electronegative nature. Transition-metal catalyzed C—H bond fluorination has significant advantages in atom-economy, reaction diversity and environmental friendliness in comparison with the traditional transition-metal catalyzed cross-coupling approaches since it obviates the use of pre-functionalized substrates. In the past decade, C—H bond fluorination strategy has emerged as a powerful protocol to access new C—F bonds. This review presents the state of art for transition-metal catalyzed C—H bond fluorination. The existing problems and limitations of the field are summarized and the outlook of the area is also prospected.
- transition-metal catalysis,
- fluorination,
- C—H bond activation,
- selective,
- directing groups
1. [1]
2. [2]
  O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308.
3. [3]
  Brooks, A. F.; Topczewski, J. J.; Ichiishi, N.; Sanford, M. S.; Scott, P. J. H. Chem. Sci. 2014, 5, 4545.
4. [4]
  Watson, D. A.; Su, M. J.; Teverovskiy G.; Zhang, Y.; García-Forta- net, J.; Kinzel T.; Buchwald, S. L. Science 2009, 325, 1661.
5. [5]
  Lee, H. G.; Milner, P. J.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 3792. (b) Milner, P. J.; Yang, Y.; Buchwald, S. L. Organometallics 2015, 34, 4775. (c) Sather, A. C.; Lee, H. G.; De La Rosa, V. Y.; Yang, Y.; Müller, P.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 13433.
6. [6]
  Furuya, T.; Ritter, T. Org. Lett.. 2009, 11, 2860.
7. [7]
  Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662.
8. [8]
  Tang, P. P.; Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 12150.
9. [9]
  Tang, P. P.; Ritter, T. Tetrahedron 2011, 67, 4449.
10. [10]
  Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 10795.
11. [11]
  Fier, P. S.; Luo, J. W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2552.
12. [12]
  Ye, Y. D.; Sanford, M. S. J. Am. Chem. Soc. 2013, 135, 4648.
13. [13]
  Ye, Y. D.; Schimler, S. D.; Hanley, P. S.; Sanford, M. S. J. Am. Chem. Soc. 2013, 135, 16292.
14. [14]
  Ichiishi, N.; Canty, A. J.; Yates, B. F.; Sanford, M. S. Org. Lett. 2013, 15, 5134.
15. [15]
  Tredwell, M.; Preshlock, S. M.; Taylor, N. J.; Gruber, S.; Huiban, M.; Passchier, J.; Mercier, J.; Génicot, C.; Gouverneur, V. Angew. Chem., Int. Ed. 2014, 53, 7751.
16. [16]
  Ichiishi, N.; Brooks, A. F.; Topczewski, J. J.; Rodnick, M. E.; Sanford, M. S.; Scott, P. J. H. Org. Lett. 2014, 16, 3224.
17. [17]
  Mu, X.; Zhang, H.; Chen, P. H.; Liu, G. S. Chem. Sci. 2014, 5, 275.
18. [18]
19. [19]
  Ball, N. D.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 3796.
20. [20]
  Furuya, T.; Kaiser, H. M.; Ritter, T. Angew. Chem., Int. Ed. 2008, 47, 5993. (b) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060. (c) Furuya, T.; Benitez, D.; Tkatchouk, E.; Strom, A. E.; Tang, P. P.; Goddard, W. A.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 3793.
21. [21]
  Lee, E.; Hooker, J. M.; Ritter, T. J. Am. Chem. Soc. 2012, 134, 17456.
22. [22]
  Xu, L. M.; Li, B. J.; Yang, Z.; Shi, Z. J. Chem. Soc. Rev. 2010, 39, 712. (b) Engle, K. M.; Mei, T. S.; Wang, X.; Yu, J. Q. Angew. Chem., Int. Ed. 2011, 50, 1478.
23. [23]
  Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134.
24. [24]
  Wang, X. S.; Mei, T. S.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 7520.
25. [25]
  Chan, K. S. L.; Wasa, M.; Wang, X. S.; Yu, J. Q. Angew. Chem., Int. Ed. 2011, 50, 9081.
26. [26]
  Chen, C. P.; Wang, C.; Zhang, J. Y.; Zhao, Y. J. Org. Chem. 2015, 80, 942.
27. [27]
  Lou, S. J.; Xu, D. Q.; Xia, A. B.; Wang, Y. F.; Liu, Y. K.; Du, X. H.; Xu, Z. Y. Chem. Commun. 2013, 49, 6218.
28. [28]
  Ding, Q. P.; Ye, C. Q.; Pu, S. Z.; Cao, B. P. Tetrahedron 2014, 70, 409.
29. [29]
  Testa, C.; Roger, J.; Scheib, S.; Fleurat-Lessard, P.; Hierso, J. C. Adv. Synth. Catal. 2015, 357, 2913.
30. [30]
  Lou, S. J.; Xu, D. Q.; Xu, Z. Y. Angew. Chem., Int. Ed., 2014, 53, 10330.
31. [31]
  Camasso, N. M.; Peérez-Temprano, M. H.; Sanford, M. S. J. Am. Chem. Soc. 2014, 136, 12771.
32. [32]
  Lou, S. J.; Chen, Q.; Wang, Y. F.; Xu, D. Q.; Du, X. H.; He, J. Q.; Mao, Y. J.; Xu, Z. Y. ACS Catal. 2015, 5, 2846.
33. [33]
  Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342.
34. [34]
  Kaspi, A. W.; Goldberg, I.; Vigalok, A. J. Am. Chem. Soc. 2010, 132, 10626.
35. [35]
  Mankad, N. P.; Toste, F. D. Chem. Sci. 2012, 3, 72.
36. [36]
  Racowski, J. M.; Gary, J. B.; Sanford, M. S. Angew. Chem., Int. Ed. 2012, 51, 3414. (b) Peérez-Temprano, M. H.; Racowski, J. M.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2014, 136, 4097.
37. [37]
  McMurtrey, K. B.; Racowski, J. M.; Sanford, M. S. Org. Lett. 2012, 14, 4094.
38. [38]
  Zhu, R. Y.; Tanaka, K.; Li, G. C.; He, J.; Fu, H. Y.; Li, S. H.; Yu, J. Q. J. Am. Chem. Soc. 2015, 137, 7067.
39. [39]
  Zhang, Q.; Yin, X. S.; Chen, K.; Zhang, S. Q.; Shi, B. F. J. Am. Chem. Soc. 2015, 137, 8219.
40. [40]
  Miao, J. M.; Yang, K.; Kurek, M.; Ge, H. B. Org. Lett. 2015, 17, 3738.
41. [41]
  Zhu, Q. H.; Ji, D. Z.; Liang, T. T.; Wang, X. Y.; Xu, Y. G. Org. Lett. 2015, 17, 3798.
42. [42]
  Fier, P. S.; Hartwig, J. F. Science 2013, 342, 956.
43. [43]
  Bloom, S.; Pitts, C. R.; Miller, D. C.; Haselton, N.; Holl, M. G.; Urheim, E.; Lectka, T. Angew. Chem., Int. Ed. 2012, 51, 10580.
44. [44]
  Bloom, S.; Pitts, C. R.; Woltornist, R.; Griswold, A.; Holl, M. G.; Lectka, T. Org. Lett. 2013, 15, 1722.
45. [45]
  Liu, W.; Huang, X. Y.; Cheng, M. J.; Nielsen, R. J.; Goddard, W. A.; Groves, J. T. Science 2012, 337, 1322
46. [46]
  Liu, W.; Groves, J. T. Angew. Chem., Int. Ed. 2013, 52, 6024.
47. [47]
  Braun, M. G.; Doyle, A. G. J. Am. Chem. Soc. 2013, 135, 12990.
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