Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3307-3313.DOI: 10.6023/cjoc202005082 Previous Articles     Next Articles


程然, 徐畅, 张新刚   

  1. 中国科学院上海有机化学研究所 分子合成卓越中心 中国科学院有机氟化学重点实验室 中国科学院大学 上海 200032
  • 收稿日期:2020-05-29 修回日期:2020-06-17 发布日期:2020-07-23
  • 通讯作者: 张新刚
  • 基金资助:

Nickel-Catalyzed Regioselective Coupling Reaction of 3,3,3-Trifluoropropene with Arylzinc Reagents

Cheng Ran, Xu Chang, Zhang Xingang   

  1. Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Shanghai 200032
  • Received:2020-05-29 Revised:2020-06-17 Published:2020-07-23
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21931013, 21672238, 21421002), and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000).

3,3,3-Trifluoropropene (TFP) is an inexpensive and bulk industrial material and has important applications in the production of fluorinated polymers, refrigerant and so on. The use of TFP as a fluorine source enables access to a variety of fluorinated compounds. To date, important progress has been made in the transformations of TFP, however, most of the developed methods focused on the functionalization of carbon-carbon double bond of TFP. The controllable formation of fluorinated products via regio-selective functionalization of TFP received less attention. Herein, a nickel-catalyzed regioselective coupling of TFP with arylzinc reagents is described. By fine-tuning the reaction solvent, two different types of fluorinated products, gem-difluoroalkenes and Heck-type aryl-substituted TFPs, were obtained. The use of dioxane as the solvent led to a series of gem-difluoroalkenes in moderate to good yields with high regio-selectivity and functional group tolerance under mild reaction conditions. While, switching solvent from dioxane to N,N-dimethylformamide (DMF), the Heck-type aryl-substituted TFPs were obtained. This regioselective coupling provides an efficient route for applications of TFP in organic synthesis.

Key words: 3,3,3-trifluoropropene, nickel catalysis, arylzinc reagents, cross-coupling