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


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