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Updated: Jun 4, 2025
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Pd/Ag-Cocatalyzed Merging Intramolecular Oxidative Coupling and Cascade [4 + 2] Cycloaddition: Synthesis and
Yu Dong1, Lin Chen1, Han-Qing Wu1
1Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, College of Chemistry and Life Science, Chengdu Normal University, Chengdu 611130, China.
Abstract:
We report a step-economic strategy for the direct synthesis of novel polycyclic N-heterocycle-fused naphthoquinones by merging intramolecular oxidative coupling and cascade [4 + 2] cycloaddition. In the protocol, mechanistic investigations suggest that the cascade reaction involves the intermediate spiro polycyclic N-heterocycles and [4 + 2] cycloaddition processes. This protocol is featured with moderate to excellent yields, wide substrate scope, and divergent structures of products. In addition, the photophysical properties of the synthesized products were evaluated. These products exhibit interesting fluorescence properties, and surprisingly, the compounds have the ability to selectively recognize trifluoroacetic acid.
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