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

• Published in: Organic letters 2024-07, Vol.26 (29), p.6230
• Main Authors: Jiang, Qin, Dong, Jianyang, Wang, Chenya, Li, Fei, Zhou, Xuechen, Wang, Yuying, Liao, Huijuan, Dang, Jiayi, Li, Gang, Xue, Dong
• Format: Article
• Language: English
• ISSN: 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.4c02171

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.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.