Light-Induced, Cs₂CO₃ Promoted C–S Cleavage of Heteroaryl Sulfones for Benzyl Heteroarylation of [1.1.1]Propellane

Abstract

In this study, we developed a light-induced difunctionalization of [1.1.1]propellane with heteroaryl sulfones acting as difunctional reagents, allowing the introduction of alkyl and heteroaryl units across bicyclo[1.1.1]pentane frameworks. It features a broad substrate scope and can be used to functionalize structurally complex natural products. Mechanistic investigations indicate the Cs 2 CO 3 promoted homolytic cleavage of heteroaryl sulfone C−S bonds by light. Moreover, the benzothiazolyl moiety in the products can serve as a formyl precursor, indicating the robust transformability of the products, owing to the ability of aldehydes to undergo a wide variety of organic transformations.