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Multicomponent Heterogeneous Semiconductor Photocatalytic Sulfinylsulfonylation of Alkenes with Alkyl Iodides and SO<sub>2</sub>

Pan Zhou, Yongxin Zhang, Jiarong Chen, Xiaoxiao Yang, Hui Xu, Xinyue Ma, Yuxin Yang, Meifang Zheng, Chao Shu

2024Organic Letters13 citationsDOI

Abstract

A multicomponent heterogeneous semiconductor photocatalytic sulfinylsulfonylation of alkenes with alkyl iodides and SO 2 was displayed under mild metal-free conditions by using boron carbonitride (BCN) as the alternative photocatalyst. This approach has resulted in the production of a wide range of structurally diverse sultine products in moderate to high yields, using readily available starting materials including alkyl iodides and olefins with broad functional group tolerance. The method is also suitable for the late-stage functionalization of complex bioactive molecules. A radical-polar crossover cyclization (RPCC) process was proposed based on mechanistic studies.

Topics & Concepts

ChemistryAlkylPhotocatalysisSemiconductorOrganic chemistryCatalysisOptoelectronicsPhysicsSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsRadical Photochemical Reactions
Multicomponent Heterogeneous Semiconductor Photocatalytic Sulfinylsulfonylation of Alkenes with Alkyl Iodides and SO<sub>2</sub> | Litcius