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铜催化及添加剂自由的芳基和杂芳基碘化物的脱羧三氟甲基化反应。

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides.

机构信息

Department of Engineering, Carbon Dioxide Activation Center (CADIAC), Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark.

出版信息

Org Biomol Chem. 2020 Feb 19;18(7):1417-1425. doi: 10.1039/c9ob02635e.

Abstract

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

摘要

一种铜催化的(杂)芳基碘代物的脱羧三氟甲基化反应已经被开发出来。重要的是,这种新的铜催化反应在没有任何配体和金属添加剂的情况下进行。该方案显示出良好的官能团耐受性,并且与杂芳环体系兼容。该反应可在 15 mmol 规模下放大,产率提高。最后,通过后期安装三氟甲基官能团,得到了抗抑郁药百忧解的 N-三氟乙酰胺变体,证明了所开发方法的适用性。

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