Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane with Katritzky Pyridinium Salts.

(Hetero)arylated bicyclo[1.1.1]pentanes (BCPs) are important for the construction of complex druglike target molecules. Herein, we developed a method for light-induced, Cs2CO3-promoted homolytic cleavage of pyridinium C-N bonds for generating alkyl radicals from amino acid-derived Katritzky salts and use of the radicals for functionalization of [1.1.1]propellane to rapidly generate (hetero)arylated BCPs. The method features excellent functional group tolerance and a broad substrate scope and can be used to functionalize structurally complex natural products.

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

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 Cs2CO3 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.