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光诱导氯代芳烃在流动中的芳基化反应:不对称联苯的合成。

Photoinduced arylation of chloroarenes in flow: synthesis of unsymmetrical biaryls.

机构信息

Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 University Road, Hsinchu 30010, Taiwan.

出版信息

Org Biomol Chem. 2022 Nov 2;20(42):8212-8216. doi: 10.1039/d2ob01710e.

Abstract

A photoflow method is presented for a radical-based coupling of unactivated arenes and aryl chlorides. The process proceeded smoothly at ambient temperature under metal-free conditions. Of note is that the reaction conditions are fine-tuned for chloroarenes with different electronic properties. While the reactivity profile of aryl chlorides is generally known to be inferior to those of the corresponding iodides and bromides, we demonstrate that the title protocol is efficient in converting readily available and inexpensive chloroarenes into unsymmetrical biaryl products.

摘要

本文提出了一种基于光流的自由基偶联方法,用于未活化的芳基和芳基氯的偶联。该过程在无金属条件下于环境温度下顺利进行。值得注意的是,反应条件经过了精细调整,以适应具有不同电子性质的氯代芳烃。虽然芳基氯的反应性通常不如相应的碘化物和溴化物,但我们证明,标题方案可有效地将易得且廉价的氯代芳烃转化为不对称联苯产物。

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