Citation: Wang Feng, Tang Pingping. Recent Advances in Trifluoromethoxylation Reactions[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 1805-1813. doi: 10.6023/cjoc202003048 shu

Recent Advances in Trifluoromethoxylation Reactions

Wang Feng ,
Tang Pingping ^,

State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Corresponding author: Tang Pingping, ptang@nankai.edu.cn
Received Date: 20 March 2020
Revised Date: 24 April 2020
Available Online: 30 April 2020
Fund Project: The National Natural Science Foundation of China 21925105Project supported by the National Key Research and Development Program of China (No. 2016YFA0602900), the National Natural Science Foundation of China (Nos. 21672110, 21925105) and the Natural Science Foundation of Tianjin City (No. 18JCJQJC47000)The Natural Science Foundation of Tianjin City 18JCJQJC47000Project supported by the National Key Research and Development Program of China 2016YFA0602900The National Natural Science Foundation of China 21672110

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In recent years, the field of organic fluorine chemistry has developed rapidly. Fluorination and fluorine-containing functionalization reactions have attracted extensive attention of organic chemists due to their special physical and chemical properties. The introduction of fluorine-containing group into drug molecules can improve the biological activity of drug molecules. Trifluoromethoxy group has strong electron absorption and high lipophilicity, compounds containing trifluoromethoxy play an important role in the fields of medicine, pesticides and materials. In recent years, some innovative strategies have been used to synthesize compounds containing trifluoromethoxy group. This account mainly focuses on the research of trifluoromethoxy reaction in our group, and some challenges faced by trifluoromethoxy reaction.
- trifluoromethoxylation,
- trifluoromethyl aryl sulfonate (TFMS),
- (E)-O-trifluoromethyl-benzaldoximes (TFBO)
1. [1]
  (a) Becker A. Inventory of Industrial Fluoro-biochemicals, Eyrolles, Paris, 1996.
  (b) Smart, B. E. J. Fluorine Chem. 2001, 109, 3.
  (c) Dunitz, J. D. ChemBioChem 2004, 5, 614.
  (d) Dolbier, W. R. J. Fluorine Chem. 2005, 126, 157.
  (e) Hird, M. Chem. Soc. Rev. 2007, 36, 2070.
  (f) Pagliaro, M.; Ciriminna R. J. Mater. Chem. 2005, 15, 4981.
  (g) Wang, J.; Snchez-Rosell, M.; AceÇa, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
  (h) Jeschke, P. ChemBioChem 2004, 5, 570.
2. [2]
  (a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
  (b) Mller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
3. [3]
  Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525. doi: 10.1021/cr60274a001
4. [4]
  Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165. doi: 10.1021/cr00002a004
5. [5]
  (a) Kapustin, E. G.; Bzhezovsky, V. M.; Yagupolskii, L. M. J. Fluorine Chem. 2002, 113, 227.
  (b) Klocker, J.; Karpfen, A.; Wolschann, P. Chem. Phys. Lett. 2003, 367, 566.
  (c) Manteau, B.; Genix, P.; Brelot, L.; Vors, J. P.; Pazenok, S.; Giornal, F.; Leuenberger, C.; Leroux, F. R. Eur. J. Org. Chem. 2010, 6043.
6. [6]
  Moujalled, D.; White, A. R. CNS Drugs 2016, 30, 227.
7. [7]
  (a) Yagupol'skii, L. M. Dokl. Akad. Nauk SSSR 1955, 105, 100.
  (b) Yarovenko, N. N.; Vasileva, A. S. Zh. Obshch. Khim. 1958, 28, 2502.
  (c) Yagupol'skii, L. M.; Troitskaya, V. I. J. Gen. Chem. USSR 1961, 31, 845.
  (d) Yagupol'skii, L. M.; Orda, V. V. Zh. Obshch. Khim. 1964, 34, 1979.
  (e) Manteau, B.; Genix, P.; Brelot, L.; Vors, J. P.; Pazenok, S.; Giornal, F.; Leuenberger, C.; Leroux, F. R. Eur. J. Org. Chem. 2010, 6043.
  (f) Sheppard, W. A. J. Org. Chem. 1964, 29, 1.
  (g) Kuroboshi, M.; Suzuki, K.; Hiyama, T. Tetrahedron Lett. 1992, 33, 4173.
  (h) Kanie, K.; Tanaka, Y.; Suzuki, K.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 471.
  (i) Kuroboshi, M.; Hiyama, T. Adv. Synth. Catal. 2001, 343, 235.
8. [8]
  For recent reviews on trifluoromethoxylation reactions, see: (a) Besset, T.; Jubault, P.; Pannecouke, X.; Poisson, T. Org. Chem. Front. 2016, 3, 1004.
  (b) Tlili, A.; Toulgoat, F.; Billard, T. Angew. Chem., Int. Ed. 2016, 57, 11726.
  (c) Lee, K. N.; Lee, J. W.; Ngai, M. Y. Tetrahedron 2018, 74, 7127.
  (d) Lee, J. W.; Lee, K. N.; Ngai, M. Y. Angew. Chem., Int. Ed. 2019, 58, 11171.
  (e) Hardy, M. A.; Chachignon, H.; Cahard, D. Asian J. Org. Chem. 2019, 8, 591.
  (f) Zhang, X. F.; Tang, P. P. Sci. China: Chem. 2019, 62, 525.
  (g) Jiang, X. H.; Tang, P. P. Chin. J. Chem. 2020, 38, 101.
9. [9]
  (a) Umemoto, T.; Adachi, K.; Ishihara, S. J. Org. Chem. 2007, 72, 6905.
  (b) Stanek, K.; Koller, R.; Togni, A. J. Org. Chem. 2008, 73, 7678.
  (c) Liang, A.; Han, S.; Liu, Z.; Wang, L.; Li, J.; Zou, D.; Wu, Y. Chem.-Eur. J. 2016, 22, 5102.
  (d) Koller, R.; Huchet, Q.; Battaglia, P.; Welch, J. M.; Togni, A. Chem. Commun. 2009, 5993.
  (e) Santschi, N.; Geissbhler, P.; Togni, A. J. Fluorine Chem. 2012, 135, 83.
  (f) Matousek, V.; Pietrasiak, E.; Sigrist, L.; Czarniecki, B.; Togni, A. Eur. J. Org. Chem. 2014, 3087.
  (g) Hojczyk, K. N.; Feng, P.; Zhan, C.; Ngai, M. Y. Angew. Chem., Int. Ed. 2014, 53, 14559.
  (h) Chu, L.; Qing, F. L. Acc. Chem. Res. 2014, 47, 1513.
  (i) Liu, J. B.; Chen, C.; Chu, L.; Chen, Z. H.; Xu, X. H.; Qing, F. L. Angew. Chem., Int. Ed. 2015, 54, 11839. (j) Liu, J. B.; Xu, X. H.; Qing, F. L. Org. Lett. 2015, 17, 5048.
  (k) Naumann, D.; Kischkewitz, J. J. Fluorine Chem. 1990, 46, 265.
  (l) Hojczyk, K. N.; Feng, P.; Zhan, C.; Ngai, M. Y. Angew. Chem., Int. Ed. 2014, 53, 14559.
  (m) Lee, K. N.; Lee, J. W.; Ngai, M. Y. Synlett 2016, 27, 313.
10. [10]
  Kellogg, K. B.; Cady, G. H. J. Am. Chem. Soc. 1948, 70, 3986. doi: 10.1021/ja01192a006
11. [11]
  Venturini, F.; Navarrini, W.; Famulari, A.; Sansotera, M.; Dardani, P.; Tortelli, V. J. Fluorine Chem. 2012, 140, 43. doi: 10.1016/j.jfluchem.2012.04.008
12. [12]
  (a) Zheng, W. J.; Morales-Rivera, C. A.; Lee, J. W.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2018, 57, 9645.
  (b) Zheng, W. J.; Lee, J. W.; Morales-Rivera, C. A.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2018, 57, 13795.
13. [13]
  Jelier, B. J.; Tripet, P. F.; Pietrasiak, E.; Franzoni, I.; Jeschke, G.; Togni, A. Angew. Chem., Int. Ed. 2018, 57, 13784.
14. [14]
  (a) Noftle, R. E.; Cady, G. H. Inorg. Chem, 1965, 4, 1010.
  (b) Katsuhara, Y.; DesMarteau, D. D. J. Am. Chem. Soc. 1980, 102, 2681.
15. [15]
  (a) Kolomeitsev, A. A.; Vorobyev, M.; Gillandt, H. Tetrahedron Lett. 2008, 49, 449.
  (b) Ignatyev, N.; Hierse, W.; Seidel, M.; Bathe, A.; Schroeter, J.; Koppe, K.; Meier, T.; Barthen, P.; Frank, W. DE 102008024221, 2009.
  (c) Ignatyev, N.; Hierse, W.; Seidel, M.; Bathe, M.; Schroeter, J.; Koppe, K.; Meier, T.; Barthen, P.; Frank, W. WO 2009141053, 2009.
  (d) Marrec, O.; Billard, T.; Vors, J. P.; Pazenok, S.; Langlois, B. R. J. Fluorine Chem. 2010, 131, 200.
  (e) Sokolenko, T. M.; Davydova, Y. A.; Yagupol'skii, Y. L. J. Fluorine Chem. 2012, 136, 20.
16. [16]
  (a) Barbion, J.; Pazenok, S.; Vors, J. P.; Langlois, B. R.; Billard, T. Org. Process Res. Dev. 2014, 18, 1037.
  (b) Chen, C. H.; Chen, P. H.; Liu, G. S. J. Am. Chem. Soc. 2015, 137, 15648.
  (c) Chen, C. H.; Luo, Y. X.; Fu, L.; Chen, P. H.; Lan, Y.; Liu, G. S. J. Am. Chem. Soc. 2018, 140, 1207.
  (d) Chen, S.; Huang, Y.; Fang, X.; Li, H.; Zhang, Z.; Hor, T. S. A.; Weng, Z. Dalton Trans. 2015, 44, 19682.
  (e) Zha, G. F.; Han, J. B.; Hu, X. Q.; Qin, H. L.; Fang, W. Y.; Zhang, C. P. Chem. Commun. 2016, 52, 7458.
  (f) Chen, D.; Lu, L.; Shen, Q. L. Org. Chem. Front. 2019, 6, 1801.
  (g) Yang, Y.; Yao, J.; Yan, W.; Luo, Z.; Tang, Z. Org. Lett. 2019, 21, 8003.
  (h) Chen, C. H.; Hou, C. Q.; Chen, P. H.; Liu, G. S. Chin. J. Chem. 2020, 38, 346.
17. [17]
  (a) Qi, X. X.; Chen, P. H.; Liu, G. S. Angew. Chem., Int. Ed. 2017, 56, 9517.
  (b) Chen, C. H.; Pfluger, P. M.; Chen, P. H.; Liu, G. S. Angew. Chem., Int. Ed. 2019, 58, 2392.
18. [18]
  (a) Farnham, W. B.; Smart, B. E.; Middleton, W. J.; Calabrese, J. C.; Dixon, D. A. J. Am. Chem. Soc. 1985, 107, 4565.
  (b) Huang, C.; Liang, T.; Harada, S.; Lee, E.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 13308.
19. [19]
  Newton, J. J.; Jilier, B. J.; Meanwell, M.; Martin, R. E.; Britton, R.; Friesen, C. M. Org. Lett. 2020, 22, 1785. doi: 10.1021/acs.orglett.0c00099
20. [20]
  Marrec, O.; Billard, T.; Vors, J.; Pazenok, P.; Langlois, B. R. Adv. Synth. Catal. 2010, 352:2831. doi: 10.1002/adsc.201000488
21. [21]
  (a) Guo, S.; Cong, F.; Guo, R.; Wang, L.; Tang, P P. Nat. Chem. 2017, 9, 546.
  (b) Jiang, X. H.; Deng, Z. J.; Tang, P. P. Angew. Chem., Int. Ed. 2018, 130, 298.
  (c) Liu, J.; Wei, Y. L.; Tang, P. P. J. Am. Chem. Soc. 2018, 140, 15194.
  (d) Cong, F.; Wei, Y. L.; Tang, P. P. Chem. Commun. 2018, 54, 4473.
  (e) Yang, H. D.; Wang, F.; Jiang, X. H.; Zhou, Y.; Xu, X. F.; Tang, P. P. Angew. Chem., Int. Ed. 2018, 57. 13266.
  (f) Wang, F.; Xu, P.; Cong, F.; Tang, P. P. Chem. Sci. 2018, 9, 8836.
  (g) Yang, S. Q.; Chen, M.; Tang, P. P. Angew. Chem., Int. Ed. 2019, 58, 7840.
22. [22]
  Zhou, M.; Ni, C.; Zeng, Y.; Hu, J. B. J. Am. Chem. Soc. 2018, 140, 6801. doi: 10.1021/jacs.8b04000
23. [23]
  Li. Y.; Yang, Y.; Xin, J. R.; Tang, P. P. Nat. Commun. 2020, 11, 755. doi: 10.1038/s41467-020-14598-1
24. [24]
  Xu, P.; Guo, S.; Wang, L. Y.; Tang, P. P. Angew. Chem., Int. Ed. 2014, 53, 5955. doi: 10.1002/anie.201400225
25. [25]
  Xu, P.; Wang, F.; Fan, G. L.; Xu, X. F.; Tang, P. P. Angew. Chem., Int. Ed. 2017, 56, 1101.
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