Photocatalytic Three-Component Synthesis of 3-Heteroarylbicyclo[1.1.1]pentane-1-acetates,Organic Letters

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Photocatalytic Three-Component Synthesis of 3-Heteroarylbicyclo[1.1.1]pentane-1-acetates
Organic Letters ( IF 4.9 ) Pub Date : 2023-05-26 , DOI: 10.1021/acs.orglett.3c01213
Wenhao Xu ₁ , Zicong Zheng ₁ , Guoxiang Bao ₁ , Yue Wang ₁ , Yan Gao ₁ , Hui Zhu ₁ , Gongcheng Xu ₁ , Yu Zhu ₁ , Chuanming Yu ₁ , Xinpeng Jiang ₁

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Herein, we report a visible-light-induced three-component reaction involving [1.1.1]propellane, diazoates, and various heterocycles for the synthesis of 3-heteroarylbicyclo[1.1.1]pentane-1-acetates. Throughout this reaction, the radicals generated from diazoate species react with [1.1.1]propellane in an addition reaction to form bicyclo[1.1.1]pentane (BCP) radicals that subsequently react with heterocycles, leading to the formation of 1,3-disubstituted BCP acetates. Notably, this methodology exhibits excellent functional group compatibility, high atom economy, and mild reaction conditions, thus facilitating suitable synthetic access to 1,3-disubstituted BCP acetates.

中文翻译：

3-杂芳基双环[1.1.1]戊烷-1-乙酸酯的光催化三组分合成

在此，我们报告了一种可见光诱导的三组分反应，涉及 [1.1.1] 丙烷、重氮酸盐和各种杂环化合物，用于合成 3-杂芳基双环 [1.1.1] 戊烷-1-乙酸酯。在整个反应过程中，重氮酸盐类物质产生的自由基在加成反应中与 [1.1.1] 丙烷反应形成双环 [1.1.1] 戊烷 (BCP) 自由基，随后与杂环反应，导致形成 1,3-双取代的 BCP 乙酸酯。值得注意的是，该方法具有出色的官能团相容性、高原子经济性和温和的反应条件，从而有助于合成 1,3-二取代的 BCP 乙酸酯。

更新日期：2023-05-26

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