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Iron-Promoted Oxidative Alkylation/Cyclization of Ynones with 4-Alkyl-1,4-dihydropyridines: Access to 2-Alkylated Indenones

Fang-Ting Xiong, Bin-Hong He, Yu Liu*, Quan Zhou and Jian-Hong Fan*

*Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China, Email:,

F.-T. Xiong, B.-H. He, Y. Liu, Q. Zhou, J.-H. Fan, J. Org. Chem., 2022, 87, 8599-8610.

DOI: 10.1021/acs.joc.2c00766

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An iron-promoted oxidative tandem alkylation/cyclization of ynones with 4-alkyl-substituted 1,4-dihydropyridines provides 2-alkylated indenones with excellent selectivity under mild conditions. The process occurs via oxidative homolysis of a C-C σ-bond in 1,4-dihydropyridines to generate an alkyl radical followed by its addition to the C-C triple bond and an intramolecular cyclization.

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proposed mechanism

Key Words

indenones, potassium peroxydisulfate

ID: J42-Y2022