Photocatalyzed reverse polarity oxidative Povarov reaction of glycine derivatives with maleimides
Photocatalyzed reverse polarity oxidative Povarov reaction of glycine derivatives with maleimides
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甘氨酸衍生物与马来酰亚胺的光催化反极性氧化Povarov反应
DOI：
10.1002/cjoc.202100401
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发表时间：
2021
影响因子：
5.4
通讯作者：
Congde Huo
中科院分区：
文献类型：
--
作者：
Yongxin Zhang;Wei‐Qun Jiang;Xiazhen Bao;Yifeng Qiu;Yong Yuan;Caixia Yang;Congde Huo
主要观察结果和结论首次实现了N-芳基甘氨酸衍生物与缺电子烯烃的氧化串联（4+2）-环化/芳构化，使用Ru（bpy）3Cl 2作为光催化剂，TBHP作为氧化剂，结合蓝光LED的可见光照射。甘氨酸衍生物的单电子氧化和随后的α-去质子化产生α-氨基烷基自由基，然后被亲电马来酰亚胺捕获。作为一种原子经济、高效的方法，在温和的反应条件下，以较高的产率合成了多种吡咯并[3，4-c]喹啉-1，3-二酮。
Main observation and conclusionAn oxidative tandem (4+2)‐cyclization/aromatization ofN‐aryl glycine derivatives with electron‐deficient alkenes was first achieved using Ru(bpy)3Cl2as a photocatalyst and TBHP as an oxidant in combination with visible‐light irradiation by blue LEDs. One‐electron oxidation and the following α‐deprotonation of glycine derivatives afford α‐amino alkyl radicals, which were then trapped by electrophilic maleimides. As an atom‐economic and efficient method, a variety of pyrrolo[3,4‐c]quinoline‐1,3‐diones have been obtained in good yields under mild reaction conditions.