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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3307 - 3313

DOI: https://doi.org/10.6023/cjoc202005082

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

  • Cheng Ran ,
  • Xu Chang ,
  • Zhang Xingang
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  • 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 date: 2020-05-29

  Revised date: 2020-06-17

  Online 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).

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Abstract

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

Cite this article

Cheng Ran , Xu Chang , Zhang Xingang . Nickel-Catalyzed Regioselective Coupling Reaction of 3,3,3-Trifluoropropene with Arylzinc Reagents[J]. Chinese Journal of Organic Chemistry, 2020 , 40(10) : 3307 -3313 . DOI: 10.6023/cjoc202005082

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