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镍催化的 1,2,3-苯并三嗪-4(3H)-酮与芳基溴化物的交叉电偶联反应。

Nickel-Catalyzed Cross-Electrophile Coupling of 1,2,3-Benzotriazin-4(3)-ones with Aryl Bromides.

机构信息

Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China.

College of Science, Hebei Agricultural University, Baoding 071000, P. R. China.

出版信息

J Org Chem. 2022 Dec 16;87(24):16567-16577. doi: 10.1021/acs.joc.2c02246. Epub 2022 Dec 1.

Abstract

The nickel-catalyzed cross-electrophile coupling of 1,2,3-benzotriazin-4(3)-ones with aryl bromides to generate a diverse array of -arylated benzamide derivatives has been developed. The reaction displayed good functional group tolerance with Zn as the reductant. The key to this transformation is the ring opening of benzotriazinones, which undergo a denitrogenative process to obtain various benzamide derivatives (29 examples, 42-93% yield). The scalability of this transformation was demonstrated.

摘要

发展了镍催化的 1,2,3-苯并三嗪-4(3)-酮与芳基溴化物的交叉电偶联反应,以生成各种芳基取代的苯甲酰胺衍生物。该反应对 Zn 作为还原剂具有良好的官能团耐受性。这种转化的关键是苯并三嗪酮的开环,其经历脱氮过程以获得各种苯甲酰胺衍生物(29 个实例,42-93%的产率)。该转化的可扩展性得到了证明。

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