化学
废止
分子内力
磺酰
光催化
串联
分子间力
甲亚胺叶立德
催化作用
组合化学
光化学
立体化学
分子
有机化学
环加成
光催化
烷基
材料科学
复合材料
1,3-偶极环加成
作者
Jie Qiu,Wei Li,Xiaofeng Li,Yongyong Cao,Cheng-Xue Pan,Huaifeng Li
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-11-01
卷期号:25 (44): 8000-8004
标识
DOI:10.1021/acs.orglett.3c03180
摘要
Azomethine imines, broadly known as 1,3-dipoles, efficiently produce synthetically and biologically significant dinitrogen-fused heterocycles via predominantly concerted or ionic pathways. Herein, we describe a radical-based annulation of azomethine imines utilizing visible-light photoredox catalysis for the first time. This strategy enables the synthesis of dinitrogen-fused saturated six-membered cyclic products that have traditionally been difficult to access. Notably, our process exhibits exceptional cis diastereoselectivity, controlled by the anomeric effect. Initial mechanistic investigations reveal a tandem process comprising intermolecular radical addition and intramolecular 6-exo-trig cyclization. This work illustrates potential within the realm of visible-light-driven radical cyclization reactions involving azomethine imines.
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