Synthesis 2021; 53(13): 2293-2303
DOI: 10.1055/a-1395-4788
paper

Efficient Monofluoroalkylation of Thiophenols or Phenols with α-Bromo-α-Fluoroketones under Mild Conditions

Authors

  • Zhi Li

    a   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
  • Mougui Fang

    a   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
  • Jingjing Wu

    a   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
    b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
  • Yunli Liu

    a   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
  • Yecheng Liu

    a   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
  • Fanhong Wu

    a   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, P. R. of China

We are grateful for financial support from the National Natural Science Foundation of China (Grant Nos. 21672151 and 21602136).


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Abstract

An efficient nucleophilic substitution reaction between α-bromo-α-fluoroketones and thiophenols or phenols is reported for the synthesis of α-fluoro-β-ketosulfides or α-fluoro-β-ketone ethers in yields ranging from 78–93%. This method exhibits good functional group tolerance and a broad scope of nucleophilic substrates, including natural phenolic compounds.

Supporting Information



Publication History

Received: 28 December 2020

Accepted after revision: 18 February 2021

Accepted Manuscript online:
18 February 2021

Article published online:
04 March 2021

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