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Photocatalytic Three-Component Synthesis of 3-Heteroarylbicyclo[1.1.1]pentane-1-acetates.

Wenhao XuZicong ZhengGuoxiang BaoYue WangYan GaoHui ZhuGongcheng XuYu ZhuChuan-Ming YuXinpeng Jiang
Published in: Organic letters (2023)
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.
Keyphrases
  • electron transfer
  • genetic diversity