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Regioselective and Diastereoselective Halofunctionalization of Alkenes Promoted by Organophotocatalytic Solar Catalysis

Huili Li, Jianmin Fu, J.‐M. FU, Xueji Li, Donglei Wei, Hou Chen, Liangjiu Bai, Lixia Yang, Huawei Yang, Wenxiang Wang

2023The Journal of Organic Chemistry10 citationsDOI

Abstract

A visible-light metal-free photocatalytic regioselective and enantioselective alkene halofunctionalization reaction under mild conditions is reported. Various terminal and internal alkenes were transformed to their α-halogenated and α,β-dibrominated derivatives in good to excellent yields within reaction time as short as 5 min. Water can be used as the "green" nucleophile and solvent in the halohydroxylation and halo-oxidation reactions. Different types of products can be obtained by adjusting the reaction conditions. In addition, sunlight is proved to produce products with similar yields, representing a practical example of solar synthesis and providing an opportunity for solar energy utilization.

Topics & Concepts

RegioselectivityAlkeneNucleophileEnantioselective synthesisChemistryCatalysisOrganic chemistryPhotocatalysisSolar energyReaction conditionsPhotochemistryCombinatorial chemistryEcologyBiologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Regioselective and Diastereoselective Halofunctionalization of Alkenes Promoted by Organophotocatalytic Solar Catalysis | Litcius