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

doi:10.6023/cjoc202005082

有机化学 ›› 2020, Vol. 40 ›› Issue (10): 3307-3313.DOI: 10.6023/cjoc202005082 上一篇下一篇

所属专题：黄乃正院士七十华诞专辑

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

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 E-mail:xgzhang@mail.sioc.ac.cn
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.

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

Cheng Ran, Xu Chang, Zhang Xingang

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).

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摘要/Abstract

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

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

引用此文

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.

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.

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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

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

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