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Electrocatalytic Cascade Selenylation/Cyclization/Deamination of 2-Hydroxyaryl Enaminones: Synthesis of 3-Selenylated Chromones under Mild Conditions

Kaili Cen, Yuan Liu, Junhong Yu, Zhouting Zeng, Qian Hou, Guojun He, Mixia Ouyang, Qiaolin Wang, Dahan Wang, Feng Zhao, Jinhui Cai

2024The Journal of Organic Chemistry39 citationsDOI

Abstract

Herein, we disclosed a highly efficient pathway toward 3-selenylated chromone derivatives via electrocatalytic cascade selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amendable to scale-up the reaction. Additionally, the preliminary experiments revealed that this reaction probably proceeded via a cation pathway instead of a radical pathway.

Topics & Concepts

ChemistryChromoneDeaminationElectrosynthesisCascade reactionCombinatorial chemistryCascadeSubstrate (aquarium)Organic chemistryCatalysisElectrochemistryEnzymeElectrodeChromatographyPhysical chemistryOceanographyGeologySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Electrocatalytic Cascade Selenylation/Cyclization/Deamination of 2-Hydroxyaryl Enaminones: Synthesis of 3-Selenylated Chromones under Mild Conditions | Litcius