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Visible-Light-Driven Photoredox-Catalyzed Three-Component Radical Cyanoalkylfluorination of Alkenes with Oxime Esters and a Fluoride Ion

Hao Qian, Jun Chen, Jun Chen, Bin Zhang, Ying Cheng, Wen‐Jing Xiao, Jia‐Rong Chen, Jia‐Rong Chen

2021Organic Letters47 citationsDOI

Abstract

A metal-free, photoredox-catalyzed three-component cyanoalkylfluorination of alkenes under mild and redox-neutral conditions is reported. This protocol features use of readily available alkenes, oxime esters, and cost-effective nucleophilic fluoride reagents, giving diverse cyanoalkylfluorinated products with generally good yields. Excellent functional group tolerance and mild reaction conditions also render this protocol suitable for cyanoalkylfluorination of pharmaceutically relevant molecule-derived alkene.

Topics & Concepts

ChemistryAlkeneOximeReagentNucleophileFluorideCatalysisCombinatorial chemistryFunctional groupPhotoredox catalysisPhotochemistryOrganic chemistryInorganic chemistryPhotocatalysisPolymerFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques