Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 177-182.DOI: 10.6023/cjoc201808041 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Articles

铜催化的芳基炔酮的羟化三氟甲硫基化反应

胡娟娟a, 黄焰根a, 徐修华b, 卿凤翎a,b   

  1. a 东华大学化学化工与生物工程学院 生态纺织教育部重点实验室 上海 201620;
    b 中国科学院上海有机化学研究所 有机氟化学重点实验室 上海 200032
  • 收稿日期:2018-08-30 修回日期:2018-10-23 出版日期:2019-01-25 发布日期:2018-11-12
  • 通讯作者: 卿凤翎 E-mail:flq@mai.sioc.ac.cn
  • 基金资助:

    国家自然科学基金(Nos.21332010,21421002)、中国科学院战略性先导科技专项(No.XDB20000000)和中国科学院青年创新促进会(No.2016234)资助项目.

Copper-Catalyzed Hydroxytrifluoromethylthiolation of Arylpropynones

Hu Juanjuana, Huang Yangena, Xu Xiuhuab, Qing Fenglinga,b   

  1. a Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620;
    b Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2018-08-30 Revised:2018-10-23 Online:2019-01-25 Published:2018-11-12
  • Contact: 10.6023/cjoc201808041 E-mail:flq@mai.sioc.ac.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21332010, 21421002), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000), and the Youth Innovation Promotion Association of the Chinese Academy of Sciences (No. 2016234).

Recently, the preparation of fluorinated compounds through difunctionalization strategies has become a hot research area in fluorine chemistry. In this work, a copper-catalyzed hydroxytrifluoromethylthiolation of arylpropynones for the synthesis of the corresponding trifluoromethylthiolated enols was developed. The copper salt and solvent are crucial to the yields of this reaction. Under optimized reaction conditions, a series of trifluoromethylthiolated enols were obtained in moderate to good yields.

Key words: copper, trifluoromethylthiolation, hydroxylation, propynone, radical