可见光促进的重氮烷与3-氨甲基化马来酰亚胺的N-H插入/可控转化
Visible-Light-Promoted N-H Insertion/Controllable Transformation of Diazoalkanes and 3-Aminomethylated Maleimides.
作者信息
Sang Qian-Qian, Chen Ze-Le, Yao Na, Xuan Jun
机构信息
Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, People's Republic of China.
Key Laboratory of Structure and Functional Regulation of Hybrid Materials, Ministry of Education, Anhui University, Hefei, Anhui 230601, People's Republic of China.
出版信息
J Org Chem. 2024 Sep 20;89(18):13608-13622. doi: 10.1021/acs.joc.4c01791. Epub 2024 Sep 5.
The utilization of photogenerated carbene species to perform N-H insertion reactions has attracted considerable attention in the past few years. In this Article, we disclose a visible-light-promoted N-H insertion of 3-aminomethylated maleimides with aryl diazoacetates under sole blue LED irradiation. Continuous flow reactor technology was exploited to improve the reaction efficiency. By simply varying the reaction conditions, the formed N-H insertion products could be selectively transferred to bioimportant octahydropyrrolo[3,4-]pyrroles and -selective trisubstituted olefins.
在过去几年中，利用光生卡宾物种进行N-H插入反应已引起了相当大的关注。在本文中，我们揭示了在单独的蓝色发光二极管照射下，3-氨甲基化马来酰亚胺与芳基重氮乙酸酯的可见光促进的N-H插入反应。利用连续流动反应器技术提高反应效率。通过简单地改变反应条件，所形成的N-H插入产物可以选择性地转化为具有生物学重要性的八氢吡咯并[3,4-]吡咯和选择性三取代烯烃。
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