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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 2: 679 - 685

DOI: https://doi.org/10.6023/cjoc202203031

Copper-Promoted Trifluoromethylthiolation of Anilines with CF3SO2Na

  • Yasir Mumtaz ,
  • Jie Liu ,
  • Xin Huang
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  • a School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094
    b Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, Jinhua, Zhejiang 321004
†(These authors contributed equally to this work).
* Corresponding author. E-mail:

Received date: 2022-07-03

  Revised date: 2022-08-30

  Online published: 2022-10-25

Supported by

National Natural Science Foundation of China(21776138); National Natural Science Foundation of China(22078161); National Natural Science Foundation of China(22108124); National Natural Science Foundation of China(21901232); Fundamental Research Funds for the Central Universities(30918011314); Fundamental Research Funds for the Central Universities(30922010403); Natural Science Foundation of Jiangsu Province(BK20141394); Qing Lan and Six Talent Peaks in Jiangsu Province

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Abstract

An inexpensive and easily accessible sodium trifluoromethyl sulfinate (CF3SO2Na) was employed as the trifluoromethylthio source, while anilines were used as the starting materials in a process for the synthesis of copper-promoted aryl(trifluoromethyl)sulfanes. Trifluoromethylthiolation of aromatic rings in one pot over two steps is made possible by the presence of a phosphine reducing agent. In the reaction, the copper salt promotes the conversion of trifluoromethylthio anion, and the reaction offers an effective and practical way to create derivatives of trifluoromethylthio substituted benzene.

Key words： aniline; sodium trifluoromethanesulfinate; phosphine reducing agent; trifluoromethylthiolation

Cite this article

Yasir Mumtaz , Jie Liu , Xin Huang . Copper-Promoted Trifluoromethylthiolation of Anilines with CF3SO2Na[J]. Chinese Journal of Organic Chemistry, 2023 , 43(2) : 679 -685 . DOI: 10.6023/cjoc202203031

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