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Updated: Apr 23, 2026
![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
Copper-Catalyzed Cascade Coupling/Cyclization/Switchable aza-Claisen Rearrangement for Indole Skeletons
Junyu Chen1, Ping Wang1, Yaowen Liu1
1Faculty of Science, Kunming University of Science and Technology, Kunming 650500, China.
None:
A copper-catalyzed cascade coupling/cyclization/switchable aza-Claisen rearrangement was disclosed for the first time, realizing the divergent synthesis of 2,3-disubstituted, C3-allylated, or C2-but-3-en-1-ylated indole derivatives from N-allyl-2 alkynylanilines and diazo compounds. Compared to previous works, the application of diazo compounds as coupling partners significantly expanded the variety of functional groups on the C2 position. Importantly, a catalytic amount of organic base, triethylamine, was found to act as a chemical switch to govern two different aza-Claisen rearrangement pathways.
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