Site-selective alkylation of electron-deficient aromatic cycles: visible-light photoredox-catalyzed radical di-functionalization of [1.1.1]propellane

Abstract

We report herein a visible-light photoredox-catalyzed three-component radical coupling of [1.1.1]propellane with electron-deficient aromatic cycles and Katritzky salts, accessing structurally diverse alkyl arylated bicyclo[1.1.1]pentanes in good isolated yields. The use of electron-deficient aromatic cycles as an aryl source was crucial for the site-selective arylation of tertiary BCP carbon radicals. The synthetic utility of the present protocol was demonstrated by a large-scale reaction and synthetic derivatization of the product.