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

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

研究论文

镍催化下3,3,3-三氟丙烯与芳基锌试剂的区域选择性偶联反应

  • 程然 ,
  • 徐畅 ,
  • 张新刚
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  • 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

  网络出版日期: 2020-07-23

基金资助

国家自然科学基金（Nos.21931013，21672238，21421002）和中国科学院先导专项（No.XDB20000000）资助项目.

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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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摘要

3，3，3-三氟丙烯是一类廉价易得的含氟工业原料，在工业生产上有着重要的应用，其巨大的应用潜力仍值得深入研究，因此探索新型反应路径对三氟丙烯的高效转化具有重要意义.报道了一种镍催化下芳基锌试剂与3，3，3-三氟丙烯高区域选择性偶联反应.通过反应溶剂的调控可以选择性生成偏氟烯烃和Heck型三氟丙烯衍生物，具有反应条件温和以及底物普适性好等特点，为3，3，3-三氟丙烯的高效转化提供了一种新的路径.

关键词： 3,3,3-三氟丙烯; 镍催化; 芳基锌试剂; 交叉偶联

本文引用格式

程然 , 徐畅 , 张新刚 . 镍催化下3,3,3-三氟丙烯与芳基锌试剂的区域选择性偶联反应[J]. 有机化学, 2020 , 40(10) : 3307 -3313 . DOI: 10.6023/cjoc202005082

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

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