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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Zn-Promoted Radical Azo-Coupling: A Halogen-Atom-Transfer-Promoted C(sp3)-N Formation
Yule Xie1, Hongli Xia1, Yi Ding1
1College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou, 311121Zhejiang, P. R. China.
Abstract:
We report a Zn-enabled radical strategy for constructing aryl-alkyl diazo compounds from aryl diazonium salts and alkyl iodides. Zn serves as a simple single-electron transfer initiator to generate aryl radicals, which undergo rapid XAT to form alkyl radicals, followed by azo coupling. The method features a broad substrate scope, good functional group tolerance, and scalability. Notably, substrates capable of 1,5-HAT deliver C-H-functionalized products, highlighting the synthetic versatility of this protocol.
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