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Dialkylzinc-Mediated Cross-Coupling Reactions of Perfluoroalkyl and Perfluoroaryl Halides with Aryl Halides

机译:全氟烷基卤化物和全氟芳基卤化物与芳基卤化物的二烷基锌介导的交叉偶联反应

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摘要

A highly chemoselective perfluoroalkylation reaction of aromatic halides is reported. Thermally stable perfluoroalkylzinc reagents, generated by a rapid halogen-zinc exchange reaction between diorganozinc and perfluoroalkyl halide species, couple with a wide range of aryl halides in the presence of a copper catalyst, in moderate to high yields. Good stability of the perfluoroalkylzinc species was indicated by DFT calculation and the reagents were storable for at least three months under argon without loss of activity. This method is applicable to gram-scale synthesis, and its functional group tolerance compares favorably with reported protocols.
机译:据报道,芳族卤化物具有高度化学选择性的全氟烷基化反应。由二有机锌与全氟烷基卤化物之间的快速卤素-锌交换反应产生的热稳定的全氟烷基锌试剂,在铜催化剂的存在下,与多种芳基卤化物偶合,产率中等至高。通过DFT计算表明全氟烷基锌物质的良好稳定性,并且该试剂在氩气下可存储至少三个月而不会损失活性。该方法适用于克级合成,其官能团耐受性优于已报道的方案。

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