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Accessing Benzoazepine Derivatives via Photoinduced Radical Relay Formal [5 + 2] Reaction of Amide/Alkyne Enabled by Palladium Catalysis

A novel class of alkyne-tethered amides facilitates an unprecedented photoinduced palladium-catalyzed radical relay formal [5 + 2] reaction. This innovative strategy allows for the rapid construction of diverse fused benzoazepine structures, yielding structurally novel and compelling compounds. With...

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Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (13), p.2662-2667
Main Authors: Du, Yu-jia, Sheng, Xia-xin, Tang, Lu-ning, Chen, Jia-ming, Liu, Guo-ying, Hu, Hao, Yang, Sen, Zhu, Lei, Chen, Ming
Format: Article
Language:English
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Summary:A novel class of alkyne-tethered amides facilitates an unprecedented photoinduced palladium-catalyzed radical relay formal [5 + 2] reaction. This innovative strategy allows for the rapid construction of diverse fused benzoazepine structures, yielding structurally novel and compelling compounds. With a broad substrate scope and excellent functional group tolerance, the methodology synthesizes biologically active compounds. Notably, the resulting tricyclic benzo­[b]­azepines offer diversification opportunities through simple transformations. DFT calculations elucidate a seven-membered ring closure mechanism involving the alkenyl radical and Pd­(I) rebound alongside a concerted metalation–deprotonation (CMD) process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00979