共轭微孔聚合物
光催化
吲哚
吲哚试验
共轭体系
微型多孔材料
组合化学
化学
催化作用
聚合物
有机化学
作者
Wei Ou,Guoqiang Zhang,Jie Wu,Chenliang Su
标识
DOI:10.1021/acscatal.9b00693
摘要
Herein, we describe a visible-light-induced radical strategy for the 1,2-formylarylation of N-arylacrylamides via the C–H activation of 1,3-dioxolane using a carbazolic-cyano conjugated microporous polymer (CC-CMP) as a metal-free photocatalyst. This process provides an efficient and mild approach for constructing highly functionalized formyl-substituted oxindoles, which are valuable building blocks that allow rapid access to various important heterocycle-fused and spirocyclic indole alkaloids. Utilizing this strategy, bioactive alkaloids, such as (±)-desoxyeseroline, (±)-esermethole, and (±)-N-Me-coerulescine, have been concisely synthesized in up to 74% overall yield from low-cost acrylamides and 1,3-dioxolane. The overall yields of our approach are much higher than those of conventional multistep methods. Gram-scale syntheses of natural alkaloids have been demonstrated, highlighting the practical utility of this protocol. The use of CC-CMP photocatalysts, which are metal-free, flexible, stable, effective, and reusable, making this strategy appealing to advanced chemical manufacturing.
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