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Updated: Apr 25, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Aryldiazonium-Salt-Triggered Radical Alkylation/Cyclization Reaction of N-Arylacrylamides via Hydrogen Atom Transfer
Ao-Yun Li1, Long-Jin Zhong1, Peng-Fei Huang1
1Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
Abstract:
Phenanthridines are a key N-heterocyclic scaffold that is widely found in numerous important functional compounds. Herein, we disclose an aryldiazonium salt-mediated radical alkylation/cyclization reaction of N-arylacrylamides with diverse C(sp3)-H partners including acetonitrile, acetone, alcohols, chlorides, cyclic alkanes, and toluene derivatives. Numerous alkylated phenanthridines are prepared with up to 77% yield without oxidants or transition-metal catalysts, showing good group tolerance. Preliminary mechanistic studies reveal that the generation of alkyl radicals proceeds through hydrogen atom transfer (HAT) between C(sp3)-H bonds and aryl radicals, which are generated in situ from aryldiazonium salts.
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