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可见光诱导喹喔啉-2(1)-酮与氟代烷基醇的需氧C3-H氟烷氧基化反应

Visible-light-induced aerobic C3-H fluoroalkoxylation of quinoxalin-2(1)-ones with fluoroalkyl alcohols.

作者信息

Xu Xiaobo, Xia Chengcai, Li Xiaojun, Sun Jian, Hao Liqiang

机构信息

Pharmacy College, Shandong First Medical University, Shandong Academy of Medical Sciences Taian 271000 China

Shanghai Synmedia Chemical Co., Ltd Shanghai 201201 China.

出版信息

RSC Adv. 2020 Jan 9;10(4):2016-2026. doi: 10.1039/c9ra10194b. eCollection 2020 Jan 8.

Abstract

A novel and efficient method of visible-light-induced C3-H fluoroalkoxylation of quinoxalin-2(1)-ones with fluoroalkyl alcohols is developed. This approach uses readily available fluoroalkyl alcohols as fluoroalkoxylation reagents and displays a wide substrate scope, providing the fluoroalkoxylated products in moderate to good yields. Compared with the previous method, such a transformation uses oxygen as an oxidant, which avoids the utilization of plenty of PhI(TFA). In addition, this strategy also gives a practical tool for the rapid synthesis of histamine-4 receptor antagonist and new N-containing bidentate ligands. A radical mechanism was suggested according to the results of control experiments.

摘要

开发了一种新颖且高效的可见光诱导喹喔啉-2(1)-酮与氟代烷基醇进行C3-H氟代烷氧基化反应的方法。该方法使用易于获得的氟代烷基醇作为氟代烷氧基化试剂,底物范围广泛,能以中等至良好的产率提供氟代烷氧基化产物。与之前的方法相比,这种转化使用氧气作为氧化剂,避免了大量使用PhI(TFA)。此外,该策略还为组胺-4受体拮抗剂和新型含氮双齿配体的快速合成提供了一种实用工具。根据对照实验结果提出了一种自由基机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3299/9047172/e7ca80f69a70/c9ra10194b-s1.jpg

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