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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 7: 2135 - 2141

DOI: https://doi.org/10.6023/cjoc202002034

Preparation of Biaryl Fluorosulfates by a Tandem Process

  • Li Xinmin ,
  • Hu Rui ,
  • Chen Zhengjun ,
  • Hu Qinghong ,
  • Yuan Zeli
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  • College of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000

Received date: 2020-02-25

  Revised date: 2020-04-26

  Online published: 2020-05-11

Supported by

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).

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Abstract

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

Key words： phenol; baryl fluorosulfates; Suzuki reaction; one-pot reaction; Pd/C

Cite this article

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

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