Citation: Wang Jian-Yong, Ma Lan, Li Yan, Wang Xi-Sheng. Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 232-237. doi: 10.6023/cjoc201807052 shu

Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons

Wang Jian-Yong ^a,b,† ,
Ma Lan ^a,† ,
Li Yan ^a ,
Wang Xi-Sheng ^a,,

a.
Hefei National Laboratory for Physical Sciences at the Microscale & Department of Chemistry, University of Science and Technology of China, Hefei 230026
b.
School of Light Industry and Engineering, Qilu University of Technology(Shandong Academy of Sciences), Jinan 250353

Corresponding author: Wang Xi-Sheng, xswang77@ustc.edu.cn

^†

Received Date: 27 July 2018
Revised Date: 25 October 2018
Available Online: 11 January 2018
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21602213, 21522208)the National Natural Science Foundation of China 21522208the National Natural Science Foundation of China 21602213

Figures(1)

Trifluoromethylthiolation/oxidation of styrenes with easiy-handling AgSCF₃ used as the trifluoromethylthiolating reagent has been described, which furnished a series of α-trifluoromethylthio acetophenons. A variety of substituted styrene could be bifunctionalized via radical process in a mixed solvent of dimethyl sulfoxide (DMSO) and CHCl₃, with potassium persulfate used as the oxidant under mild conditions. A simple and efficent method for the facile construction of various α-trifluoromethylthio acetophenons is thus demonstrated.
- styrene,
- trifluoromethylthiolation,
- radical
1. [1]
2. [2]
  (a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525.
  (b) Yagupol'skii, L. M.; Il'chenko, A. Y.; Kondratenko, N. V. Russ. Chem. Rev. 1974, 43, 32.
  (c) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
  (d) Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827.
  (e) Manteau, B.; Pazenok, S.; Vors, J. P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140.
3. [3]
  (a) Yarovenko, N. N.; Vasileva, A. S. J. Gen. Chem. USSR (Engl. Transl.) 1958, 28, 2537.
  (b) Nodiff, E.; Lipschutz, A. S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60.
  (c) Feiring, A. E. J. Org. Chem. 1979, 44, 2907.
4. [4]
  (a) Billard, T.; Blond, G.; Langlois, B. R. Tetrahedron Lett. 1997, 38, 65.
  (b) Billard, T.; Blond, G.; Langlois, B. R. Tetrahedron Lett. 2001, 42, 2473.
  (c) Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754.
5. [5]
6. [6]
  (a) Chen, Q.-Y.; Duan, J.-X. J. Chem. Soc., Chem. Commun. 1993, 918.
  (b) Zhang, C.-P.; Vicic, D. A. Chem. Asian J. 2012, 7, 1756.
  (c) Chen, C.; Chu, L.-L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 12454.
  (d) Weng, Z.; He, W.; Chen, C.; Lee, R.; Dan, D.; Lai, Z.; Kong, D.; Yuan, Y.; Huang, K.-W. Angew. Chem., Int. Ed. 2013, 52, 1548.
7. [7]
  Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312. doi: 10.1002/anie.v50.32
8. [8]
  Chen, C.; Xie, Y.; Chu, L.; Wang, R.-W.; Zhang, X.; Qing, F. L. Angew. Chem., Int. Ed. 2012, 51, 2492. doi: 10.1002/anie.v51.10
9. [9]
  Zhang, C. P.; Vicic, D. A. J. Am. Chem. Soc. 2012, 134, 183. doi: 10.1021/ja210364r
10. [10]
  (a) Shao, X.; Wang, X.-Q.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457.
  (b) Pluta, R.; Nikolaienko, P.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 1650.
11. [11]
  Yin, G.; Kalvet, I.; Englert, U.; Schoenebeck, F. J. Am. Chem. Soc. 2015, 137, 4164. doi: 10.1021/jacs.5b00538
12. [12]
  Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128. doi: 10.1021/ol403739w
13. [13]
  Ma, L.; Cheng, X.-F.; Li, Y.; Wang, X.-S. Tetrahedron Lett. 2016, 57, 2972. doi: 10.1016/j.tetlet.2016.05.086
14. [14]
  (a) Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Chem. Commun. 2011, 47, 6632.
  (b) Lu, Q.-Q.; Liu, C.; Huang, Z.-Y.; Ma, Y.-Y.; Zhang, J.; Lei, A.-W. Chem. Commun. 2014, 50, 14101.
  (c) Wang, F.; Wang, D.-H.; Mu, X.; Chen, P.-H.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202.
15. [15]
  (a) Huang, Y.-J.; He, X.; Lin, X.-X.; Rong, M.-G.; Weng, Z.-Q. Org. Lett. 2014, 16, 3284.
  (b) Huang, Y.-J.; He, X.; Li, H.-H.; Weng, Z.-Q. Eur. J. Org. Chem. 2014, 7324.
  (c) Li, J.; Xie, F.-F.; Wang, P.-Q.; Wu, Q.-Y.; Chen, W.-D.; Ren, J.-M.; Zeng, B.-B. Tetrahedron 2015, 71, 5520.
  (d) Wang, Y.-G.; You, Y.; Weng, Z.-Q. Org. Chem. Front. 2015, 2, 574.
  (e) Wu, C.-Y.; Huang, Y.-J.; Chen, Z.-R.; Weng, Z.-Q. Tetrahedron Lett. 2015, 56, 3838.
16. [16]
  (a) Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316.
  (b) Alazet, S.; Zimmer, L.; Billard, T. Chem.-Eur. J. 2014, 20, 8589.
17. [17]
  Yadav, A. K.; Singh, K. N. Chem. Commun. 2018, 54, 1976. doi: 10.1039/C7CC09953C
18. [18]
  Arimori, S.; Takada, M.; Shibata, N. Org. Lett. 2015, 17, 1063. doi: 10.1021/acs.orglett.5b00057
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