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

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Iron-Promoted Oxidative Alkylation/Cyclization of Ynones with 4-Alkyl-1,4-dihydropyridines: Access to 2-Alkylated Indenones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-15 , DOI: 10.1021/acs.joc.2c00766
Fang-Ting Xiong ₁ , Bin-Hong He ₁ , Yu Liu ₁ , Quan Zhou ₁ , Jian-Hong Fan ₁

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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.

中文翻译：

4-烷基-1,4-二氢吡啶对茚酮的铁促进氧化烷基化/环化：获得 2-烷基化茚酮

描述了一种铁促进的氧化串联烷基化/环化 4-烷基取代的 1,4-二氢吡啶，用于有效合成 2-烷基化茚酮。该过程通过1,4-二氢吡啶中的 C-C σ-键的氧化均裂产生烷基自由基，然后在 ynone 中添加 C-C 三键和分子内环化。广泛的烷基自由基可以有效地转移以生成一系列合成有用的 2-烷基化茚酮，在温和条件下具有优异的选择性。

更新日期：2022-06-15

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