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喹喔啉-2(1H)-酮的无金属可见光诱导C(sp)-C(sp)偶联——C-N键的氧化裂解

Metal-free visible-induced C(sp)-C(sp) coupling of quinoxalin-2()-ones oxidative cleavage of the C-N bond.

作者信息

Wu Mei, Lian Nancheng, Wu Cuimin, Wu Xinyao, Chen Houzheng, Lin Chen, Zhou Sunying, Ke Fang

机构信息

Institute of Materia Medica, School of Pharmacy, Fujian Provincial Key Laboratory of Natural Medicine Pharmacology, Fujian Medical University Fuzhou 350122 China

Department of Spinal Surgery, The First Affiliated Hospital of Fujian Medical University Fuzhou 350005 China.

出版信息

RSC Adv. 2023 Jun 16;13(27):18328-18331. doi: 10.1039/d3ra03479h. eCollection 2023 Jun 15.

Abstract

A C(sp)-C(sp) reaction between aromatic hydrazines and quinoxalines has been developed through a photocatalytic system. The protocol is established for C(sp)-N bond cleavage and direct C(sp)-H functionalization for the coupling of C(sp)-C(sp) photocatalysis under mild and ideal air conditions without the presence of a strong base and metal. The mechanistic studies reveal that the generation of a benzene radical the oxidative cleavage of aromatic hydrazines for the cross-coupling of C(sp)-C(sp) with the assistance of a photocatalyst is essential. The process exhibits excellent compatibility with functional groups and provides convenient access to various 3-arylquinoxalin-2(1)-ones in good to excellent yields.

摘要

通过光催化体系开发了一种芳基肼与喹喔啉之间的C(sp)-C(sp)反应。该方案是为在温和且理想的空气条件下,在不存在强碱和金属的情况下进行C(sp)-N键裂解以及直接C(sp)-H官能化以实现C(sp)-C(sp)光催化偶联而建立的。机理研究表明,苯自由基的生成、在光催化剂的辅助下芳基肼的氧化裂解以实现C(sp)-C(sp)的交叉偶联是至关重要的。该过程对官能团具有出色的兼容性,并能以良好至优异的产率方便地合成各种3-芳基喹喔啉-2(1)-酮。

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