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Updated: Feb 27, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Photoredox-Catalyzed Modular Synthesis of ε-Lactams via Acrylamides Cyclization Enabled by Radical-Polar
Yangjing Xu1,2, Denghui Ma3, Haoran Huang1
1State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, China.
Abstract:
A photocatalytic strategy for the direct synthesis of naphtho-fused ε-lactams from acrylamides is reported. This protocol leverages visible-light-induced single-electron-transfer oxidation of acrylamides to radical cations, followed by intramolecular electrophilic aromatic substitution and subsequent functionalization with external electrophiles. This methodology facilitates the one-step construction of functionalized ε-lactam derivatives with atom and step-economy. Notably, it demonstrates good compatibility with alternative electrophiles, including allyl bromide and aryl aldehydes, and further supports downstream product derivatization, thereby underscoring its significant potential for application in the synthesis of complex molecules. Mechanistic studies confirm a radical pathway involving 1,5-hydrogen atom transfer and carbanion intermediates, presenting a novel approach to lactam scaffolds.
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