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可见光诱导的电子供体-受体介导的喹喔啉-2(1)-酮与未活化芳基碘的C-3偶联反应

Visible Light-Induced Electron-Donor-Acceptor-Mediated C-3 Coupling of Quinoxalin-2(1)-ones with Unactivated Aryl Iodides.

作者信息

Singh Nihal, Sharma Anoop, Singh Jitender, Pandey Amar Prakash, Sharma Anuj

机构信息

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India.

出版信息

Org Lett. 2024 Aug 2;26(30):6471-6476. doi: 10.1021/acs.orglett.4c02296. Epub 2024 Jul 23.

Abstract

Visible light-induced C-3 arylation of quinoxalin-2(1)-ones with abundantly available aryl iodides with good yields via an electron-donor-acceptor (EDA)-complex formation have been accomplished. The radical scavenging, Electron paramagnetic resonance (EPR), UV-visible experiments, density functional theory (DFT), and quantum yield studies revealed that the reaction went through a radical pathway via a single electron transfer (SET) process. Furthermore, the protocol could also be applied to the synthesis of biologically active molecules, illustrating the practicality of the present protocol.

摘要

通过形成电子给体-受体(EDA)络合物,实现了可见光诱导喹喔啉-2(1)-酮与大量可得的芳基碘发生C-3芳基化反应,产率良好。自由基清除、电子顺磁共振(EPR)、紫外-可见光谱实验、密度泛函理论(DFT)和量子产率研究表明,该反应通过单电子转移(SET)过程经由自由基途径进行。此外,该方法还可应用于生物活性分子的合成,证明了本方法的实用性。

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