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-芳基芳基硫代磺酸酯与醋酸铜介导的2-芳基吡啶和杂芳烃的芳基硫醇化反应

-Aryl Arenesulfonothioate and Copper Acetate Mediated Arylthiolation of 2-Arylpyridines and Heteroarenes.

作者信息

Sharma Poonam, Jain Nidhi

机构信息

Department of Chemistry , Indian Institute of Technology , New Delhi 110016 , India.

出版信息

J Org Chem. 2019 Oct 18;84(20):13045-13052. doi: 10.1021/acs.joc.9b01954. Epub 2019 Sep 19.

Abstract

Copper acetate mediated regioselective -arylthiolation of 2-arylpyridines has been accomplished for the first time using -aryl arenesulfonothioate as the arylthiolating agent. The reaction shows good functional group tolerance and gives thioarylated products in 67-89% yields. This reagent is a good alternative to unpleasant smelling arylthiols. Experimental evidence suggests an unprecedented insertion of an arylthio unit from both parts of the reagent (SPh and -TolSO) in the presence of copper acetate. Indoles and imidazopyridines also undergo facile reaction at the C-3 position and furnish thioarylated derivatives in good yields.

摘要

首次使用芳基芳基磺酰硫酯作为芳基硫醇化试剂,实现了醋酸铜介导的2-芳基吡啶的区域选择性芳基硫醇化反应。该反应具有良好的官能团耐受性,硫芳基化产物的产率为67-89%。该试剂是有难闻气味的芳基硫醇的良好替代品。实验证据表明,在醋酸铜存在下,试剂的两个部分(SPh和-TolSO)会发生前所未有的芳基硫单元插入反应。吲哚和咪唑并吡啶在C-3位也能轻松反应,以良好的产率提供硫芳基化衍生物。

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