Citation: Lu Shiyao, Chen Wenbo, Shen Qilong. Friedel-Crafts trifluoromethylthiolation of electron-rich (hetero)arenes with trifluoromethylthio-saccharin in 2, 2, 2-trifluoroethanol (TFE)[J]. Chinese Chemical Letters, ;2019, 30(12): 2279-2281. doi: 10.1016/j.cclet.2019.07.060 shu

Friedel-Crafts trifluoromethylthiolation of electron-rich (hetero)arenes with trifluoromethylthio-saccharin in 2, 2, 2-trifluoroethanol (TFE)

Lu Shiyao ^a ,
Chen Wenbo ^a,*, ,
Shen Qilong ^b,*,

a.
Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, Shanghai University of Electric Power, Shanghai 200090, China
b.
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China

wenbochen@shiep.edu.cn

shenql@mail.sioc.ac.cn

Received Date: 11 April 2019
Revised Date: 14 July 2019
Accepted Date: 29 July 2019
Available Online: 30 December 2019

Figures(2)

A promoter-free Friedel-Crafts trifluoromethylthiolation of electron-rich arenes and heteroarenes with N-trifluoromethylthiosaccharin 5 using 2, 2, 2-trifluoroethanol (TFE) as the solvent was described. The reactions were conducted at 40℃ and a variety of common functional groups were compatible.
- Fluorine,
- Trifluoromethylthio,
- Friedel-crafts,
- Arene,
- Trifluoroethanol
1. [1]
  S. Purser, P.R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 37 (2008) 320-330. doi: 10.1039/B610213C
2. [2]
  N.A. Meanwell, J. Med. Chem. 54 (2011) 2529-2591. doi: 10.1021/jm1013693
3. [3]
  Y. Zhou, J. Wang, Z.N. Gu, et al., Chem. Rev. 116 (2016) 422-518. doi: 10.1021/acs.chemrev.5b00392
4. [4]
  G. Landelle, A. Panossian, S. Pazenok, J.P. Vors, F.R. Leroux, Beilstein J. Org. Chem. 9 (2013) 2476-2536. doi: 10.3762/bjoc.9.287
5. [5]
  T. Liang, C.N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 52 (2013) 8214-8264. doi: 10.1002/anie.201206566
6. [6]
  X.X. Shao, C.F. Xu, L. Lu, Q. Shen, Acc. Chem. Res. 48 (2015) 1227-1236. doi: 10.1021/acs.accounts.5b00047
7. [7]
  X.H. Xu, K. Matsuzaki, N. Shibata, Chem. Rev. 115 (2015) 731-764. doi: 10.1021/cr500193b
8. [8]
  H. Chachignon, D. Cahard, Chin. J. Chem. 34 (2016) 445-454. doi: 10.1002/cjoc.201500890
9. [9]
  P.P. Zhang, L. Lu, Q. Shen, Acta Chim. Sin. 75 (2017) 744-769. doi: 10.6023/A17050202
10. [10]
  Y. Guo, M.W. Huang, X.L. Fu, et al., Chin. Chem. Lett. 28 (2017) 719-728. doi: 10.1016/j.cclet.2017.02.006
11. [11]
  S. Andreades, J.F. Harris, W.A. Sheppard Jr., J. Org. Chem. 29 (1964) 898-900. doi: 10.1021/jo01027a034
12. [12]
  CF₃SCl was reported to have an L(ct)50 of between 440 and 880 ppm min^-1, Chem. Eng. News 45 (1967) 44, doi: http://dx.doi.org/10.1021/cen-v045n044.p042a.
13. [13]
  R. Honeker, J.B. Ernst, F. Glorius, Chem. -Eur. J. 21 (2015) 8047-8051. doi: 10.1002/chem.201500957
14. [14]
  J. Ernst, L. Rakers, F. Glorius, Synthesis 49 (2017) 260-268.
15. [15]
  A. Ferry, T. Billard, E. Bacqué, B.R. Langlois, J. Fluorine Chem. 134 (2012) 160-163. doi: 10.1016/j.jfluchem.2011.02.005
16. [16]
  Y.D. Yang, A. Azuma, E. Tolunaga, et al., J. Am. Chem. Soc. 135 (2013) 8782-8785. doi: 10.1021/ja402455f
17. [17]
  Z.Y. Huang, Y.D. Yang, E. Tokunaga, N. Shibata, Org. Lett. 17 (2015) 1094-1097. doi: 10.1021/ol503616y
18. [18]
  B.Q. Ma, X.X. Shao, Q. Shen, J. Fluorine Chem. 171 (2015) 73-77. doi: 10.1016/j.jfluchem.2014.09.011
19. [19]
  X.X. Shao, C.F. Xu, L. Lu, Q. Shen, Org. Chem. 80 (2015) 3012-3021. doi: 10.1021/jo502645m
20. [20]
  C.F. Xu, B.Q. Ma, Q. Shen, Angew. Chem. Int. Ed. 53 (2014) 9316-9320. doi: 10.1002/anie.201403983
21. [21]
  P.P. Zhang, M. Li, X.S. Xue, et al., J. Org. Chem. 81 (2016) 7486-7509. doi: 10.1021/acs.joc.6b01178
22. [22]
  L. Jiang, J. Qian, W. Yi, et al., Angew. Chem. Int. Ed. 54 (2015) 14965-14969. doi: 10.1002/anie.201508495
23. [23]
  L. Jiang, W. Yi, Q. Liu, Adv. Synth. Catal. 358 (2016) 3700-3705. doi: 10.1002/adsc.201600651
24. [24]
  L. Jiang, Q. Yan, R. Wang, et al., Chem. -Eur. J. 24 (2018) 18749-18756. doi: 10.1002/chem.201804027
25. [25]
  M. Bu, G. Lu, C. Cai, Org. Chem. Front. 4 (2017) 266-270. doi: 10.1039/C6QO00622A
26. [26]
  X. Zhao, A. Wei, B. Yang, et al., J. Org. Chem. 82 (2017) 9175-9181. doi: 10.1021/acs.joc.7b01226
27. [27]
  H. Chachignon, M. Maeno, H. Kondo, N. Shibata, D. Cahard, Org. Lett. 18 (2016) 2467-2470. doi: 10.1021/acs.orglett.6b01026
28. [28]
  K. Lu, Z. Deng, M. Li, T. Li, X. Zhao, Org. Biomol. Chem. 15 (2017) 1254-1260. doi: 10.1039/C6OB02465C
29. [29]
  X. Zhao, X. Zheng, M. Tian, et al., Tetrahedron 73 (2017) 7233-7238. doi: 10.1016/j.tet.2017.11.019
30. [30]
  L. Ma, X.F. Cheng, Y. Li, X.S. Wang, Tetrahedron Lett. 57 (2016) 2972-2975. doi: 10.1016/j.tetlet.2016.05.086
31. [31]
  P. Trillo, A. Baeza, C. Naj'era, J. Org. Chem. 77 (2012) 7344-7354. doi: 10.1021/jo301049w
32. [32]
  G.X. Li, J. Qu, Chem. Commun. 46 (2010) 2653-2655. doi: 10.1039/b926684d
33. [33]
  P.A. Champagne, Y. Benhassine, J. Desroches, J.F. Paquin, Angew. Chem. Int. Ed. 53 (2014) 13835-13839. doi: 10.1002/anie.201406088
34. [34]
  N. Weisner, M.G. Khaledi, Green Chem. 18 (2016) 681-685. doi: 10.1039/C5GC01463H
35. [35]
  R.H. Vekariya, J. Aubé, Org. Lett. 18 (2016) 3534-3537. doi: 10.1021/acs.orglett.6b01460
1. [1]
  Jia-Ru Li , Ning Li , Li-Ling He , Jun He . Fluorine-functionalized zirconium-organic cages for efficient photocatalytic oxidation of thioanisole. Chinese Chemical Letters, 2025, 36(1): 109934-. doi: 10.1016/j.cclet.2024.109934
2. [2]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
3. [3]
  Qian Wang , Yeping Bian , Gagan Dhawan , Wei Zhang , Alexander E. Sorochinsky , Ata Makarem , Vadim A. Soloshonok , Jianlin Han . FDA approved fluorine-containing drugs in 2023. Chinese Chemical Letters, 2024, 35(11): 109780-. doi: 10.1016/j.cclet.2024.109780
4. [4]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
5. [5]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
6. [6]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
7. [7]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
8. [8]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
9. [9]
  Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
10. [10]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
11. [11]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(567)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142