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Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides

Jinhui Cai, Kaili Cen, Weishuang Li, Hongyi Lin, Haixia Zhang

2024Advanced Synthesis & Catalysis17 citationsDOIOpen Access PDF

Abstract

Abstract Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization of ynamides was disclosed. A series of diaryl diselenides, dialkyl diselenides, and heteroaryl‐substituted ynamides was tolerated in this protocol and delivered 4‐selenyloxazolones in 28–83% yields. The scale‐up reaction and the oxidation of selenylated‐oxazolone was performed to showcase the practicability of this method. Furthermore, mechanistic experiments indicated that a cationic pathway instead of a radical pathway was probably involved.

Topics & Concepts

ChemistryElectrochemistryCombinatorial chemistryOrganic chemistryElectrodePhysical chemistryCatalytic Alkyne ReactionsSulfur-Based Synthesis TechniquesOrganic Chemistry Cycloaddition Reactions