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铜催化 -二氟烯丙基与芳基硼酸酯的脱氟芳基化反应合成烯丙基单氟化物。

Copper Catalyzed Defluoroarylation of -Difluoroallenes to Allenyl Monofluorides with Aryl Boronic Esters.

机构信息

School of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, P. R. China.

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China.

出版信息

Org Lett. 2023 Jun 23;25(24):4546-4550. doi: 10.1021/acs.orglett.3c01583. Epub 2023 Jun 8.

Abstract

Few studies have been performed on allenyl monofluorides, especially on aryl-substituted frames, due to concerns about their stability. Here we report a copper-catalyzed regioselective synthesis of such structures with inexpensive and accessible aryl boronic esters under mild conditions. Arylated allenyl monofluorides were stable enough to be isolated and easily converted to various other fluorine-containing blueprints. Preliminary asymmetric attempts demonstrate that the reaction could proceed via a selective β-fluorine elimination process.

摘要

由于对烯丙基单氟化物,尤其是芳基取代物的稳定性的担忧,目前很少有研究涉及到它们。在这里,我们报道了一种在温和条件下,使用廉价易得的芳基硼酸酯作为底物,通过铜催化实现此类结构的区域选择性合成的方法。芳基烯丙基单氟化物的稳定性足以使其被分离出来,并很容易转化为各种其他含氟蓝图。初步的不对称尝试表明,该反应可以通过选择性的β-氟消除过程进行。

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