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Updated: Jun 3, 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
Decarboxylative-Derived 2-Aminoallyl Cations in Copper-Catalyzed Spirocyclization of Naphthols and Indoles
Shao-Chuan Li1, Huanshi Wang2, Zhifei Zhao2
1Anhui Provincial Key Laboratory of Green Carbon Chemistry, School of Chemistry & Materials Engineering, Fuyang Normal University, Fuyang 236037, PR China.
Abstract:
The dearomatization reactions of indoles or naphthols with 2-aminoallyl cations generated from ethynyl methylene carbamates (EMCCs) for the concise synthesis of spirocyclic compounds represent a significant challenge. This difficulty stems from the substantial energy barrier associated with the initial disruption of aromaticity. Nonetheless, a diverse array of spirocyclic compounds can be prepared in moderate to good yields (69-92%) under mild reaction conditions. This synthetic protocol exhibits notable advantages, including a broad substrate scope, excellent functional group tolerance, and simple operational procedures. Furthermore, scale-up experiments and late-stage functionalization studies have further underscored the practical synthetic value of this methodology. Finally, in terms of the reaction mechanism, besides the cyclization reaction, it also involves a 1,5-hydrogen shift, which constructs an unexpected cyclized compound structure and enhances the interest of the research.
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