Citation: Li Xinmin, Hu Rui, Chen Zhengjun, Hu Qinghong, Yuan Zeli. Preparation of Biaryl Fluorosulfates by a Tandem Process[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 2135-2141. doi: 10.6023/cjoc202002034 shu

Preparation of Biaryl Fluorosulfates by a Tandem Process

College of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000

Corresponding author: Li Xinmin, lixm@zmu.edu.cn Yuan Zeli, zlyuan@zmu.edu.cn
Received Date: 25 February 2020
Revised Date: 26 April 2020
Available Online: 11 May 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 81660575, 81360471), the Natural Science and Technology Foundation of Guizhou Province (No. [2018]1187), and the International Cooperation Project of Guizhou Province (No. [2020]4104)the Natural Science and Technology Foundation of Guizhou Province [2018]1187the International Cooperation Project of Guizhou Province [2020]4104the National Natural Science Foundation of China 81660575the National Natural Science Foundation of China 81360471

The one-pot tandem protocol for the preparation of biaryl fluorosulfates from bromo phenols was developed. Using Pd/C as catalyst, K₂CO₃ as base and aqueous ethanol as solvent, the Suzuki reaction was carried out at room temperature, then SO₂F₂ gas was added to the mixture to afford biaryl fluorosulfates product. The intermediate was not isolated, and phosphine ligand and nitrogen protection were not required during the reaction, which made the protocol more convenient to operate. The one-pot protocol could tolerate a range of functional groups and provided a highest product yield up to 97.2% at room temperature. Furthermore, Pd/C catalyst could be recycled and reused three times without significant loss of catalytic activity
- phenol,
- baryl fluorosulfates,
- Suzuki reaction,
- one-pot reaction,
- Pd/C
1. [1]
  Liu, Z.; Li, J.; Li, S.; Li, G.; Sharpless, K. B.; Wu, P. J. Am. Chem. Soc. 2018, 140, 2919. doi: 10.1021/jacs.7b12788
2. [2]
  (a) Revathi, L.; Ravindar, L.; Leng, J.; Rakesh, K. P.; Qin, H.-L. Asian J. Org. Chem. 2018, 7, 662.
  (b) Ravindar, L.; Bukhari, S.; Rakesh, K.; Manukumar, H.; Vivek, H.; Mallesha, N.; Xie, Z. Z.; Qin, H. L. Bioorg. Chem. 2018, 81, 107.
3. [3]
  Dong, J.; Krasnova, L.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2014, 53, 9430. doi: 10.1002/anie.201309399
4. [4]
  Veryser, C.; Demaerel, J.; Bieliuunas, V.; Gilles, P.; De Borggraeve, W. M. Org. Lett. 2017, 19, 5244.
5. [5]
  Zhou, H.; Mukherjee, P.; Liu, R.; Evrard, E.; Wang, D.; Humphrey, J. M.; Butler, T. W.; Hoth, L. R.; Sperry, J. B.; Sakata, S. K.; Helal, C. J.; Am Ende, C. W. Org. Lett. 2018, 20, 812. doi: 10.1021/acs.orglett.7b03950
6. [6]
  Guo, T.; Meng, G.; Zhan, X.; Yang, Q.; Ma, T.; Xu, L.; Sharpless, K. B.; Dong, J. Angew. Chem., Int. Ed. 2018, 57, 2605.
7. [7]
8. [8]
9. [9]
  (a) Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
  (b) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722.
10. [10]
  (a) Hirakawa, T.; Uramoto, Y.; Mimura, D.; Takeda, A.; Yanagi- sawa, S.; Ikeda, T.; Inagaki, K.; Morikawa, Y. J. Phys. Chem. B 2017, 121, 164.
  (b) Lennox, A. J. J.; Lloyd-Jones, G. C. Chem. Soc. Rev. 2014, 43, 412.
  (c) Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2116.
  (d) Amatore, C.; Duc, G. L.; Jutand, A. Chem.-Eur. J. 2013, 19, 10082.
11. [11]
  (a) Fu, L.; Cao, X.; Wan, J.; Liu, Y. Chin. J. Chem. 2020, 38, 254.
  (b) Deraedt, C.; Astruc, D. Acc. Chem. Res. 2014, 47, 494.
12. [12]
  (a) Peng, L.; Hu, Z.; Tang, Z.; Jiao, Y.; Xu, X. Chin. Chem. Lett. 2019, 30, 1481.
  (b) Xiong, J.; Zhong, G.; Zou, L.; Liu, Y. ChemistrySelect 2018, 3, 8291.
  (c) Chen, X.; Hu, C.; Wan, J. P.; Liu, Y. Tetrahedron Lett. 2016, 57, 5116.
  (d) Buchspies, J.; Szostak, M. Catalysts 2019, 9, 53.
13. [13]
  (a) Campeau, L. C.; Hazari, N. Organometallics 2019, 38, 3.
  (b) Liu, C.; Li, X. Chem. Rec. 2016, 16, 84.
14. [14]
  Liu, C.; Liu, C.; Li, X. M.; Gao, Z. M.; Jin, Z. L. Chin. Chem. Lett. 2016, 5, 631.
15. [15]
  Ma, C.; Zhao, C. Q.; Xu, X. T.; Li, Z. M.; Wang, X. Y.; Zhang, K.; Mei, T. S. Org. Lett. 2019, 21, 2464. doi: 10.1021/acs.orglett.9b00836
16. [16]
  Schimler, S. D.; Cismesia, M. A.; Hanley, P. S.; Froese, R. D. J.; Jansma, M. J.; Bland, D. C.; Sanford, M. S. J. Am. Chem. Soc. 2017, 139, 1452. doi: 10.1021/jacs.6b12911
17. [17]
  Li, X.; Feng, F.; Ren, C.; Teng, Y.; Hu, Q.; Yuan, Z. Synlett 2019, 30, 2131. doi: 10.1055/s-0039-1690227
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