可见光介导喹喔啉-2(1H)-酮C3-H缩醛化反应
收稿日期: 2022-09-11
修回日期: 2022-10-03
网络出版日期: 2022-10-25
基金资助
新疆普通高等学校天然产物化学与应用重点实验室基金(2022YSHXZD01)
Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones
Received date: 2022-09-11
Revised date: 2022-10-03
Online published: 2022-10-25
Supported by
Foundation of University and College Key Laboratory of Natural Product Chemistry and Application in Xinjiang(2022YSHXZD01)
报道了一种可见光介导1,2,3,5-四(咔唑-9-基)-4,6-二氰基苯(4CzIPN)催化喹喔啉-2(1H)-酮与乙缩醛酸的C3-H脱羧乙缩醛反应合成3-乙缩醛基喹喔啉-2(1H)-酮的方法. 该反应采用空气为氧化剂, 在室温下实现了一系列3-乙缩醛基喹喔啉-2(1H)-酮的绿色构建, 反应具有能源清洁、条件温和、非金属参与和氧化剂绿色等优点. 自由基捕捉实验和荧光猝灭实验表明, 该反应涉及光诱导自由基反应历程.
关键词： 可见光; 喹喔啉-2(1H)-酮; 脱羧缩醛化; 自由基反应
张孟琪 , 南光明 , 赵晓辉 , 魏伟 . 可见光介导喹喔啉-2(1H)-酮C3-H缩醛化反应[J]. 有机化学, 2022 , 42(12) : 4315 -4322 . DOI: 10.6023/cjoc202209013
Visible-light-mediated 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) catalyzed decarboxylic acetalation of quinoxalin-2(1H)-ones with glyoxylic acid acetalde to access 3-acetal quinoxalin-2(1H)-ones has been reported. This reaction provides a green and efficient approach to construct a series of 3-acetal quinoxalin-2(1H)-ones by using of air as the oxidant at room temperature, which has the advantages of clean source of energy, mild conditions, metal-free and green oxidant. Radical trapping experiment and fluorescence quenching experiments showed that visible-light promoted radical reaction process was involved in this reaction system.
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