Citation: Ouyang Yao, Xu Xiuhua, Qing Fengling. Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF₃[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3426-3430. doi: 10.6023/cjoc202005022 shu

Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF₃

Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Qing Fengling, flq@mail.sioc.ac.cn
Received Date: 9 May 2020
Revised Date: 3 June 2020
Available Online: 8 June 2020
Fund Project: the National Natural Science Foundation of China 21991211Project supported by the National Natural Science Foundation of China (Nos. 21421002, 21991211) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000)the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000the National Natural Science Foundation of China 21421002

Figures(2)

A silver-mediated oxidative coupling reaction of arylboronic acids with fluoroform-derived AgCF₃ using K₂S₂O₈ as oxidant was developed. This reaction provides a new route to trifluoromethylated arenes.
- oxidative trifluoromethylation,
- arylboronic acids,
- fluoroform,
- trifluoromethyl silver
1. [1]
  (a) Purser, S.; Moor, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
  (b) Cametti, M.; Crousse, B.; Metrangolo, P.; Milani, R.; Resnati, G. Chem. Soc. Rev. 2012, 41, 31.
  (c) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; delPozo, C. A.; Sorochinsky, E.; Fustero, S. V.; Soloshonok, A.; Liu, H. Chem. Rev. 2014, 114, 2432.
  (d) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.
2. [2]
  (a) Mullard, A. Nat. Rev. Drug Discovery 2018, 17, 81.
  (b) Mullard, A. Nat. Rev. Drug Discovery 2019, 18, 85.
  (c) Mullard, A. Nat. Rev. Drug Discovery 2020, 19, 79.
3. [3]
4. [4]
  For selected examples, see: (a) Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909.
  (b) Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.
  (c) Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem., Int. Ed. 2011, 50, 1896.
  (d) Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229.
  (e) Li, X.; Zhao, J.; Zhang, L.; Hu, M.; Wang, L.; Hu, J. Org. Lett. 2015, 17, 298.
  (f) Wei, Y.; Yu, L.; Lin, J.; Zheng, X.; Xiao, J. Chin. J. Chem. 2016, 34, 481.
  (g) Le, C.; Chen, T. Q.; Liang, T.; Zhang, P.; MacMillan, D. W. C. Science 2018, 360, 1010.
5. [5]
  (a) Danoun, G.; Bayarmagnai, B.; Grunberg, M. F.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 7972.
  (b) Wang, X.; Xu, Y.; Mo, F.; Ji, G.; Qiu, D.; Feng, J.; Ye, Y.; Zhang, S.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 10330.
  (c) Dai, J.-J.; Fang, C.; Xiao, B.; Yi, J.; Xu, J.; Liu, Z.-J.; Lu, X.; Liu, L. Fu, Y. J. Am. Chem. Soc. 2013, 135, 8436.
  (d) Lishchynskyi, A.; Berthon, G.; Grushin, V. V. Chem. Commun. 2014, 50, 10237.
  (e) Zhang, K.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2015, 80, 7658.
  (f) Hong, J.; Wang, G.; Huo, L.; Zheng, C. Chin. J. Chem. 2017, 35, 1761.
6. [6]
  Ye, F.; Berger, F.; Jia, H.; Ford, J.; Wortman, A.; Börgel, J.; Genicot, C.; Ritter, T. Angew. Chem., Int. Ed. 2019, 58, 14615. doi: 10.1002/anie.201906672
7. [7]
  (a) Yang, J.-Y.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2015, 180, 175.
  (b) Yang, J.-Y.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2016, 186, 45.
  (c) Pandey, V. K.; Anbarasan, P. RSC Adv. 2016, 6, 18525.
8. [8]
9. [9]
  (a) Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060.
  (b) Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174.
  (c) Jiang, X.; Chu, L.; Qing, F.-L. J. Org. Chem. 2012, 77, 1251.
  (d) Nguyen, T. V.; Ong, T. D.; Lam, A. H. M.; Pham, V. T.; Phan, N. T. S.; Truong, T. Mol. Catal. 2017, 436, 60.
10. [10]
  (a) Xu, J.; Luo, D.-F.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300.
  (b) Zhang, C.-P.; Cai, J.; Zhou, C.-B.; Wang, X.-P.; Zheng, X.; Gu, Y.-C.; Xiao, J.-C. Chem. Commun. 2011, 47, 9516.
  (c) Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342.
11. [11]
  (a) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.
  (b) Ye, Y.; Künzi, S. A.; Sanford, M. S. Org. Lett. 2012, 14, 4979.
  (c) Li, Y.; Wu, L.; Neumann, H.; Beller, M. Chem. Commun. 2013, 49, 2628.
12. [12]
  (a) Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767.
  (b) van der Born, D.; Sewing, C.; Herscheid, J. D. M.; Windhorst, A. D.; Orru, R. V. A.; Vugts, D. J. Angew. Chem., Int. Ed. 2014, 53, 11046.
  (c) Ivashkin, P.; Lemonnier, G.; Cousin, J.; Grégoire, V.; Labar, D.; Jubault, P.; Pannecoucke, X. Chem.-Eur. J. 2014, 20, 9514.
13. [13]
  (a) Zhang, S.-L.; Bie, W.-F. Dalton Trans. 2016, 45, 17588.
  (b) Zhang, S.-L.; Bie, W.-F. RSC Adv. 2016, 6, 70902.
  (c) Zhang, S.-L.; Xiao, C.; Wan, H.-X. Dalton Trans. 2018, 47, 4779.
  (d) Xiao, C.; Zhang, S.-L. Dalton Trans. 2019, 48, 848.
14. [14]
  Xiang, J.-X.; Ouyang, Y.; Xu, X.-H.; Qing, F.-L. Angew. Chem., Int. Ed. 2019, 58, 10320. doi: 10.1002/anie.201905782
15. [15]
  (a) Liu, J.-B.; Chen, C.; Chu, L.; Chen, Z.-H.; Xu, X.-H.; Qing, F.-L. Angew. Chem., Int. Ed. 2015, 54, 11839.
  (b) Liu, J.-B.; Xu, X.-H.; Qing, F.-L. Org. Lett. 2015, 17, 5048.
  (c) Fu, M.-L.; Liu, J.-B.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2017, 82, 3702.
  (d) Zhang, K.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2017, 196, 24.
  (e) Xiang, J.-X.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2017, 203, 110.
  (f) Zhu, S.-Q.; Liu, Y.-L.; Li, H.; Xu, X.-H.; Qing, F.-L. J. Am. Chem. Soc. 2018, 140, 11613.
16. [16]
  (a) Tyrra, W.; Naumann, D. J. Fluorine Chem. 2004, 125, 823.
  (b) Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955.
17. [17]
  (a) Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464.
  (b) Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713.
  (c) Wu, X.; Chu, L.; Qing, F.-L. Angew. Chem., Int. Ed. 2013, 52, 2198.
  (d) Mao, Z.; Huang, F.; Yu, H.; Chen, J.; Yu, Z.; Xu, Z. Chem.-Eur. J. 2014, 20, 3439.
  (e) Lin, J.-S.; Liu, X.-G.; Zhu, X.-L.; Tan, B.; Liu, X.-Y. J. Org. Chem. 2014, 79, 7084.
  (f) Teng, F.; Cheng, J.; Bolm, C. Org. Lett. 2015, 17, 3166.
  (g) Wu, Y.-B.; Lu, G.-P.; Yuan, T.; Xu, Z.-B.; Wan, L.; Cai, C. Chem. Commun. 2016, 52, 13668.
  (h) Harris, C. F.; Kuehner, C. S.; Bacsa, J.; Soper, J. D. Angew. Chem., Int. Ed. 2018, 57, 1311.
18. [18]
  (a) Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229.
  (b) de Salinas, S. M.; Mudarra, Á. L.; Benet-Buchholz, J.; Parella, T.; Maseras, F.; Pérez-Temprano, M. H. Chem.-Eur. J. 2018, 24, 11895.
19. [19]
  (a) Fukuyama, T.; Nishikawa, T.; Ruy, I. Eur. J. Org. Chem. 2020, 1424.
  (b) Deng, Y.; Lu, F.; You, S.; Xia, T.; Zheng, Y.; Lu, C.; Yang, G.; Chen, Z.; Gao, M.; Lei, A. Chin. J. Chem. 2019, 37, 817.
  (c) Wang, H.; Wang, J.; Qiu, W.; Yang, F.; Liu, X.; Tang, J. Chin. J. Chem. 2010, 28, 2416.
  (d) Lin, L.; Hou, C.; Li, H.; Weng, Z. Chem.-Eur. J. 2016, 22, 2075.
  (e) Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2002, 327.
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Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF3

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Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF₃