Direct Construction of Fused/Bridged 3D Rings via Visible-Light Induced Dearomative Cycloaddition of Arenes,Advanced Synthesis & Catalysis

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Direct Construction of Fused/Bridged 3D Rings via Visible-Light Induced Dearomative Cycloaddition of Arenes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-29 , DOI: 10.1002/adsc.202201110
Guangjin Zhen ₁ , Guohui Zeng ₂ , Furong Wang ₃ , Xiaohui Cao ₄ , Biaolin Yin ₁

Affiliation

Three-dimensional aliphatic fused and bridged rings are key pharmacophores in drugs and bioactive natural products. Here, we reported an organocatalytic visible-light induced dearomative cycloaddition of (hetero)arenes, with organic light-emitting diode material 4CzIPN or readily accessible thioxanthone as photocatalyst. A series of cyclobutane-fused polycyclic structures and bridged bicyclo scaffolds were prepared in reasonable yields (27–99% yield) with medium to excellent diastereoselectivity (1.4:1 to>20:1 dr), predictable regioselectivity, good functional group compatibilities and broad substrate scopes. The combination of experimental and computational studies supported the energy transfer pathways.

中文翻译：

通过可见光诱导芳烃脱芳环加成直接构建稠合/桥接 3D 环

三维脂肪族稠环和桥环是药物和生物活性天然产物中的关键药效团。在这里，我们报道了有机催化可见光诱导的（杂）芳烃脱芳环加成反应，有机发光二极管材料 4CzIPN 或易于获得的噻吨酮作为光催化剂。以合理的产率（27-99% 产率）制备了一系列环丁烷稠合多环结构和桥接双环支架，具有中等至优异的非对映选择性（1.4:1 至>20:1 dr）、可预测的区域选择性、良好的官能团相容性和广泛的应用底物范围。实验和计算研究的结合支持能量转移途径。

更新日期：2022-11-29

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