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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 7: 2018 - 2025

DOI: https://doi.org/10.6023/cjoc202003035

Copper-Catalyzed Arylated Etherification of 2,2-Difluoroethanol and Its Mechanistic Study

  • Huang Shuaishuai ,
  • Nie Yixue ,
  • Yang Jingjing ,
  • Zheng Zhanjiang ,
  • Cao Jian ,
  • Xu Zheng ,
  • Xu Liwen
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  • a Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121;
    b Collaborative Innovation Center for Fluorosilicone-based Fine Chemicals and Materials, Hangzhou Normal University, Hangzhou 311121

Received date: 2020-03-14

  Revised date: 2020-04-17

  Online published: 2020-04-23

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21703051, 21801056) and the Hangzhou Science and Technology Bureau of China (No. 20180432B05).

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Abstract

Both organofluorine and organosilicon compounds are one of the most important types of high-tech product in elementorganic chemistry, and have been received much attetions in the past decades. Considering the imporatance of difluoroethanol moeity in pesticides, the development of a mild and efficient copper-catalyzed arylated etherification reaction of difluoroethanol is highly desirable. Herein, a mild and efficient method for the preparation of difluoroethyl aryl ethers was developed by the copper-catalyzed Ullmann-type arylated etherification reaction of aryl bromides or iodides with 2,2-difluoroethanol. This reaction proceeds smoothly in the presence of CuI and 8-hydroxyquinoline/t-BuOK, and has a broad substrate scope. ESI-MS analysis supported the existence of LCu(Ⅲ)Ar(OR) species during this catalytic reaction. Further density functional theory (DFT) calculations suggest a proposed mechanism of arylated etherification reaction involving oxidative addition, followed by nucleophile substitution and reductive elimination would be rational.

Key words： Ullmann reaction; Cu-catalyzed; fluorinated compound; DFT calculation; 8-hydroxyquinoline

Cite this article

Huang Shuaishuai , Nie Yixue , Yang Jingjing , Zheng Zhanjiang , Cao Jian , Xu Zheng , Xu Liwen . Copper-Catalyzed Arylated Etherification of 2,2-Difluoroethanol and Its Mechanistic Study[J]. Chinese Journal of Organic Chemistry, 2020 , 40(7) : 2018 -2025 . DOI: 10.6023/cjoc202003035

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