Citation: 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 shu

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

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

Corresponding author: Zhang Xingang, xgzhang@mail.sioc.ac.cn
Received Date: 29 May 2020
Revised Date: 17 June 2020
Available Online: 22 July 2020
Fund Project: the National Natural Science Foundation of China 21931013the National Natural Science Foundation of China 21672238the National Natural Science Foundation of China 21421002Project 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)the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000

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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.
- 3, 3, 3-trifluoropropene,
- nickel catalysis,
- arylzinc reagents,
- cross-coupling
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