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

Org Lett. 2023 Jun 9;25(22):4050-4055. doi: 10.1021/acs.orglett.3c01213. Epub 2023 May 26.

Abstract

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.

MeSH terms

  • Acetates*
  • Light
  • Pentanes*

Substances

  • pentane
  • Pentanes
  • Acetates