Citation: Xin Wang, Zhichuan Wang, Zhenjian Li, Kai Sun. Trifluoromethoxylation/trifluoromethylthiolation/trifluoro-methylselenolation strategy for the construction of heterocycles[J]. Chinese Chemical Letters, ;2023, 34(5): 108045. doi: 10.1016/j.cclet.2022.108045 shu

Trifluoromethoxylation/trifluoromethylthiolation/trifluoro-methylselenolation strategy for the construction of heterocycles

Xin Wang ^{a, 1} ,
Zhichuan Wang ^{a, 1} ,
Zhenjian Li ^b ,
Kai Sun ^{a, *,}

a.
College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
b.
State Key Laboratory of Tree Genetics and Breeding, Research Institute of Forestry, Chinese Academy of Forestry, Beijing 100091, China

Author Bio: Xin Wang was born in Heilongjiang, China and received her MS degree from Northeast Normal University in 2012. In July 2013, she joined the College of Chemistry and Chemical Engineering, Anyang Normal University. In 2019, she pursued her Ph.D. degree in Zhengzhou University. Her research program is drug design, structural identification and structural modification of natural products
Zhichuan Wang was born in Jiangsu, China in 1997. In 2015, he began his studies at the School of Pharmacy, Jilin Medical University. In 2020, he pursued his MS degree in YanTai University under the direction of associate professor Kai Sun. His current research is focused on radical CH functionalization
Zhenjian Li, Doctor, Forestry Research Institute, China Academy of Forestry, Associate researcher, Master's supervisor. He mainly engage in the research on the components and functions of medicinal Dendrobium; Collection and development of ornamental and medicinal Dendrobium germplasm resources
Kai Sun was born in Shanxi, China in 1983. He received his Ph.D. degree in organic chemistry from Northeast Normal University in 2013 under the supervision of Prof. Qian Zhang. In July 2020, he joined the College of Chemistry and Chemical Engineering, YanTai University, where he is an professor. His current research is focused on CH functionalization, radical chemistry and organic selenium chemistry

sunk468@nenu.edu.cn

Received Date: 31 October 2022
Revised Date: 3 December 2022
Accepted Date: 5 December 2022
Available Online: 8 December 2022

Figures(39)

The XCF₃ groups (X = O, S, Se) play an increasingly important role in modern organic chemistry due to their unique electronegativity, lipophilic nature, metabolic stability, and bioavailability. Heterocyclic compounds are important scaffolds in many bioactive compounds and drugs. The incorporation of XCF₃ groups into heterocyclic compounds can change their physicochemical and biological properties, which injects new vitality into the application of heterocyclic compounds in many fields such as organic chemistry, the pharmaceutical chemistry, and life sciences. In this paper, the recent progress in the synthesis of F₃CX-containing heterocycles is reviewed, and the application scope and mechanism of some reactions are discussed.
- Trifluoromethoxylation,
- Trifluoromethylthiolation,
- Trifluoromethylselenolation,
- Cyclization
1. [1]
  K. Müller, C. Faeh, F. Diederich, Science 317 (2007) 1881–1886. doi: 10.1126/science.1131943
2. [2]
  E.P. Gillis, K.J. Eastman, M.D. Hill, et al., J. Med. Chem. 58 (2015) 8315–8359. doi: 10.1021/acs.jmedchem.5b00258
3. [3]
  S. Tang, Y.L. Deng, J. Li, et al., J. Org. Chem. 80 (2015) 12599–12605. doi: 10.1021/acs.joc.5b01803
4. [4]
  S.W. Wang, J. Yu, Q.Y. Zhou, et al., ACS Sustain. Chem. Eng. 7 (2019) 10154–10162. doi: 10.1021/acssuschemeng.9b02178
5. [5]
  Y. Ogawa, E. Tokunaga, O. Kobayashi, et al., iScience 23 (2020) 101467. doi: 10.1016/j.isci.2020.101467
6. [6]
  H.B. Mei, A.M. Remete, Y.P. Zou, et al., Chin. Chem. Lett. 31 (2020) 2401–2413. doi: 10.1016/j.cclet.2020.03.050
7. [7]
  Y.J. Yu, A.Y. Liu, G. Dhawan, et al., Chin. Chem. Lett. 32 (2021) 3342–3354. doi: 10.1016/j.cclet.2021.05.042
8. [8]
  X. Wang, J. Lei, Y.J. Liu, et al., Org. Chem. Front. 8 (2021) 2079–2109. doi: 10.1039/d0qo01629b
9. [9]
  N. Chen, J. Lei, Z.C. Wang, et al., Chin. J. Org. Chem. 42 (2022) 1061–1084. doi: 10.6023/cjoc202109033
10. [10]
  A. Leo, C. Hansch, D. Elkins, Chem. Rev. 71 (1971) 525–616. doi: 10.1021/cr60274a001
11. [11]
  C. Hansch, A. Leo, R.W. Taft, Chem. Rev. 91 (1991) 165–195. doi: 10.1021/cr00002a004
12. [12]
  Q. Glenadel, E. Ismalaj, T. Billard, Eur. J. Org. Chem. 2017 (2017) 530–533. doi: 10.1002/ejoc.201601526
13. [13]
  Y.Y. Xie, Y.C. Wang, H.E. Qu, et al., Adv. Synth. Catal. 356 (2014) 3347–3355. doi: 10.1002/adsc.201400315
14. [14]
  Y.H. Lv, J.P. Meng, C. Li, et al., Adv. Synth. Catal. 363 (2021) 5235–5265. doi: 10.1002/adsc.202101184
15. [15]
  X. Wang, Y. Zhang, K. Sun, et al., Chin. J. Org. Chem. 41 (2021) 4588–4609. doi: 10.6023/cjoc202109046
16. [16]
  H. Sheng, Q. Liu, F. Chen, et al., Chin. Chem. Lett. 33 (2022) 4298–4302. doi: 10.1016/j.cclet.2022.01.028
17. [17]
  X. Wang, J. Lei, S. Guo, et al., Chem. Commun. 58 (2022) 1526–1529. doi: 10.1039/d1cc06323e
18. [18]
  M.W. Yu, Z. Zhou, Y.W. Chen, et al., Org. Lett. 24 (2022) 4886–4891. doi: 10.1021/acs.orglett.2c01680
19. [19]
  J. Njardarson, Top 200 brand name drugs by retail sales in 2021. https://njardarson.lab.arizona.edu/sites/njardarson.lab.arizona.edu/files/Top%20200%20Pharmaceuticals%202021V2.pdf.
20. [20]
  X.H. Xu, K. Matsuzaki, N. Shibata, Chem. Rev. 115 (2015) 731–764. doi: 10.1021/cr500193b
21. [21]
  M. Li, J. Guo, X.S. Xue, J.P. Cheng, Org. Lett. 18 (2016) 264–267. doi: 10.1021/acs.orglett.5b03433
22. [22]
  X.H. Yang, D. Chang, R. Zhao, L. Shi, Asian J. Org. Chem. 10 (2021) 61–73. doi: 10.1002/ajoc.202000575
23. [23]
  X.H. Jiang, P.P. Tang, Chin. J. Chem. 39 (2021) 255–264. doi: 10.1002/cjoc.202000465
24. [24]
  K.N. Lee, J.W. Lee, M.Y. Ngai, Tetrahedron 74 (2018) 7127–7135. doi: 10.1016/j.tet.2018.09.020
25. [25]
  Y. Cao, N.Y. Xu, A. Issakhov, et al., J. Fluor. Chem. 252 (2021) 109901. doi: 10.1016/j.jfluchem.2021.109901
26. [26]
  Y.M. Li, J.F. Fu, L.Q. He, et al., RSC Adv. 11 (2021) 24474–24486. doi: 10.1039/D1RA02606B
27. [27]
  B. Sahoo, M.N. Hopkinson, Angew. Chem. Int. Ed. 57 (2018) 7942–7944. doi: 10.1002/anie.201804939
28. [28]
  J.W. Lee, K.N. Lee, M.Y. Ngai, Angew. Chem. Int. Ed. 58 (2019) 11171–11181. doi: 10.1002/anie.201902243
29. [29]
  M. Hamzehloo, A. Hosseinian, S. Ebrahimiasl, et al., J. Fluor. Chem. 224 (2019) 52–60. doi: 10.1016/j.jfluchem.2019.05.004
30. [30]
  M.A. Hardy, H. Chachignon, D. Cahard, Asian J. Org. Chem. 8 (2019) 591–609. doi: 10.1002/ajoc.201900004
31. [31]
  A.L. Barthelemy, E. Magnier, Guillaume Dagousset, Synthesis (Mass) 50 (2018) 4765–4776. doi: 10.1055/s-0037-1611278
32. [32]
  A. Hassanpour, M.R.P. Heravi, A. Ebadi, et al., J. Fluor. Chem. 245 (2021) 109762. doi: 10.1016/j.jfluchem.2021.109762
33. [33]
  H.N. Wang, J.Y. Dong, J. Shi, C.P. Zhang, Tetrahedron 99 (2021) 132476. doi: 10.1016/j.tet.2021.132476
34. [34]
  D. Louvel, C. Ghiazza, V. Debrauwer, et al., Chem. Rec. 21 (2021) 417–426. doi: 10.1002/tcr.202000184
35. [35]
  Y.D. Yang, A. Azuma, E. Tokunaga, et al., J. Am. Chem. Soc. 135 (2013) 8782–8785. doi: 10.1021/ja402455f
36. [36]
  Q. Wang, Z.S. Qi, F. Xie, X.W. Li, Adv. Synth. Catal. 357 (2015) 355–360. doi: 10.1002/adsc.201400717
37. [37]
  Q. Wang, F. Xie, X.W. Li, J. Org. Chem. 80 (2015) 8361–8366. doi: 10.1021/acs.joc.5b00940
38. [38]
  Z.Y. Huang, Y.D. Yang, E. Tokunaga, N. Shibata, Org. Lett. 17 (2015) 1094–1097. doi: 10.1021/ol503616y
39. [39]
  H. Chachignon, M. Maeno, H. Kondo, et al., Org. Lett. 18 (2016) 2467–2470. doi: 10.1021/acs.orglett.6b01026
40. [40]
  M.J. Bu, G.P. Lua, C. Cai, Org. Chem. Front. 4 (2017) 266–270. doi: 10.1039/C6QO00622A
41. [41]
  D.W. Sun, X. Jiang, M. Jiang, et al., Eur. J. Org. Chem. 2018 (2018) 2078–2081. doi: 10.1002/ejoc.201800249
42. [42]
  J.Y. Guo, R.H. Dai, W.C. Xu, et al., Chem. Commun. 54 (2018) 8980–8982. doi: 10.1039/C8CC04600J
43. [43]
  L.Q. Jiang, Q. Yan, R.K. Wang, et al., Chem. Eur. J. 24 (2018) 18749–18756. doi: 10.1002/chem.201804027
44. [44]
  F. Yin, X.S. Wang, Org. Lett. 16 (2014) 1128–1131. doi: 10.1021/ol403739w
45. [45]
  L.P. Zhu, G.Q. Wang, Q.P. Guo, et al., Org. Lett. 16 (2014) 5390–5393. doi: 10.1021/ol502624z
46. [46]
  N. Fuentes, W.Q. Kong, L. Fernandez-Sanchez, et al., J. Am. Chem. Soc. 137 (2015) 964–973. doi: 10.1021/ja5115858
47. [47]
  D.P. Jin, P. Gao, D.Q. Chen, et al., Org. Lett. 18 (2016) 3486–3489. doi: 10.1021/acs.orglett.6b01702
48. [48]
  X. Liu, R. An, X.L. Zhang, et al., Angew. Chem. Int. Ed. 55 (2016) 5846–5850. doi: 10.1002/anie.201601713
49. [49]
  J. Luo, Y.N. Liu, X.D. Zhao, Org. Lett. 19 (2017) 3434–3437. doi: 10.1021/acs.orglett.7b01392
50. [50]
  S. Pan, Y.G. Huang, X.H. Xu, F.L. Qing, Org. Lett. 19 (2017) 4624–4627. doi: 10.1021/acs.orglett.7b02249
51. [51]
  G. Dagousset, C. Simon, E. Anselmi, et al., Chem. Eur. J. 23 (2017) 4282–4286. doi: 10.1002/chem.201700734
52. [52]
  Y.M. Ren, Q.Q. Yan, Y. Li, et al., J. Org. Chem. 87 (2022) 8773–8781. doi: 10.1021/acs.joc.2c00623
53. [53]
  X.Y. Chen, C.C. Pei, B. Liu, et al., Chem. Commun. 58 (2022) 8674–8677. doi: 10.1039/d2cc02171d
54. [54]
  L. Wang, L. Xie, Z.G. Fang, et al., Org. Chem. Front. 9 (2022) 3061–3067. doi: 10.1039/D2QO00207H
55. [55]
  W. Zheng, J.W. Lee, C.A. Morales-Rivera, et al., Angew. Chem. Int. Ed. 57 (2018) 13795–13799. doi: 10.1002/anie.201808495
56. [56]
  Z.J. Deng, M.X. Zhao, F. Wang, P.P. Tang, Nat. Commun. 11 (2020) 2569–2577. doi: 10.1038/s41467-020-16451-x
57. [57]
  C.H. Chen, P.H. Chen, G.S. Liu, J. Am. Chem. Soc. 137 (2015) 15648–15651. doi: 10.1021/jacs.5b10971
58. [58]
  J.B. Liu, C. Chen, L.L. Chu, et al., Angew. Chem. Int. Ed. 54 (2015) 11839–11842. doi: 10.1002/anie.201506329
59. [59]
  P.J. Feng, K.N. Lee, J.W. Lee, et al., Chem. Sci. 7 (2016) 424–429. doi: 10.1039/C5SC02983J
60. [60]
  A.P. Liang, S.J. Han, Z.W. Liu, et al., Chem. Eur. J. 22 (2016) 5102–5106. doi: 10.1002/chem.201505181
61. [61]
  K. Sun, S.N. Wang, R. R, Feng, et al., Org. Lett. 21 (2019) 2052–2055. doi: 10.1021/acs.orglett.9b00240
62. [62]
  K. Sun, X. Wang, C. Li, et al., Org. Chem. Front. 7 (2020) 3100–3119. doi: 10.1039/d0qo00849d
63. [63]
  X. Wang, J.P. Meng, D.Y. Zhao, et al., Chin. Chem. Lett. 34 (2023) 107736. doi: 10.1016/j.cclet.2022.08.016
64. [64]
  H.F. Shi, X.Z. Wang, X.X. Li, et al., Org. Lett. 24 (2022) 2214–2219. doi: 10.1021/acs.orglett.2c00563
65. [65]
  C. Ghiazza, M. Ndiaye, A. Hamdi, et al., Tetrahedron Lett. 74 (2018) 6521–6526. doi: 10.1016/j.tet.2018.09.048
66. [66]
  X. Zhao, X.F. Wei, M.M. Tian, et al., Tetrahedron Lett. 60 (2019) 1796–1799. doi: 10.1016/j.tetlet.2019.06.002
67. [67]
  Q.Y. Han, C.L. Zhao, T. Dong, et al., Org. Chem. Front. 6 (2019) 2732–2737. doi: 10.1039/c9qo00631a
68. [68]
  A.D. Zordo-Banliat, L. Barthélémy, F. Bourdreux, et al., Eur. J. Org. Chem. 2020 (2020) 506–509.
69. [69]
  J.Y. Liu, M.M. Tian, A.K. Li, et al., Tetrahedron Lett. 66 (2021) 152809. doi: 10.1016/j.tetlet.2020.152809
70. [70]
  K.L. Tan, H.N. Wang, T. Dong, C.P. Zhang, Org. Biomol. Chem. 19 (2021) 5368–5376. doi: 10.1039/d1ob00842k
71. [71]
  Q. Glenadel, E. Ismalaj, T. Billard, Org. Lett. 20 (2018) 56–59. doi: 10.1021/acs.orglett.7b03338
72. [72]
  H. Wang, Y.F. Yao, Z.P. Zhang, et al., J. Org. Chem. 87 (2022) 3605–3612. doi: 10.1021/acs.joc.1c03156
73. [73]
  L.H. Lu, X.J. Zhao, W. Dessie, et al., Org. Biomol. Chem. 20 (2022) 1754–1758. doi: 10.1039/d1ob02402g
74. [74]
  H. Wang, Y.F. Yao, Y. You, et al., Org. Biomol. Chem. 20 (2022) 2115–2120. doi: 10.1039/d2ob00063f
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