A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source,Synlett

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A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source
Synlett ( IF 1.7 ) Pub Date : 2019-01-30 , DOI: 10.1055/s-0037-1612080
Min Zhang ₁ , Jinling Su , Yan Zhang , Mingren Chen , Weiming Li , Xuewei Qin , Yanping Xie , Lixiao Qin , Shihua Huang

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A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX2 alone or with ZnX2) promoted halogenation with N-halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X+) by the coordination of copper or zinc with the N-halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.

中文翻译：

使用 N-卤代琥珀酰亚胺作为卤化物源的铜卤化物促进香豆素的区域选择性卤化

据报道，使用金属卤化物（单独的 CuX2 或与 ZnX2）促进卤化，以 N-卤代琥珀酰亚胺（NXS）作为卤化物源，安全、方便和区域选择性地合成 3-卤香豆素。该合成涉及通过铜或锌与 N-卤代琥珀酰亚胺的配位以及随后缺电子香豆素的亲电芳香取代，在原位稳定生成高活性正卤素 (X+)。该程序也适用于以中等至定量产率卤化含电子量较低的萘醌、黄酮和甲氧基补骨脂素。该协议具有简单的实验条件，使用容易获得的廉价试剂，并为一些有用的杂芳族化合物的氯化或溴化提供了方便的方法。

更新日期：2019-01-30

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