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

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

An iron-promoted oxidative tandem alkylation/cyclization of ynones with 4-alkyl-substituted 1,4-dihydropyridines for the efficient synthesis of 2-alkylated indenones is described. The process occurs via oxidative homolysis of a C–C σ-bond in 1,4-dihydropyridines to generate an alkyl radical followed...

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Veröffentlicht in:Journal of organic chemistry 2022-07, Vol.87 (13), p.8599-8610
Hauptverfasser: Xiong, Fang-Ting, He, Bin-Hong, Liu, Yu, Zhou, Quan, Fan, Jian-Hong
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container_issue 13
container_start_page 8599
container_title Journal of organic chemistry
container_volume 87
creator Xiong, Fang-Ting
He, Bin-Hong
Liu, Yu
Zhou, Quan
Fan, Jian-Hong
description An iron-promoted oxidative tandem alkylation/cyclization of ynones with 4-alkyl-substituted 1,4-dihydropyridines for the efficient synthesis of 2-alkylated indenones is described. The process occurs via oxidative homolysis of a C–C σ-bond in 1,4-dihydropyridines to generate an alkyl radical followed by the addition of C–C triple bonds in ynones and intramolecular cyclization. A wide range of alkyl radicals could be efficiently transferred to generate a series of synthetically useful 2-alkylated indenones with excellent selectivity under mild conditions.
doi_str_mv 10.1021/acs.joc.2c00766
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title Iron-Promoted Oxidative Alkylation/Cyclization of Ynones with 4‑Alkyl-1,4-dihydropyridines: Access to 2‑Alkylated Indenones
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