Electrochemical Synthesis of 3-Selenyl-Chromones via Domino C(sp2)-H Bond Selenylation/Annulation of Enaminones
João M. Brito, Isabella M. e Oliveira, Cassio A. O. Moraes, Alex R. Schneider, Tiago E. A. Frizon, Giancarlo V. Botteselle, Vijay P. Singh, André L. Stein, Gleison A. Casagrande, Giuseppe A. Camara, Antonio L. Braga, Jamal Rafique, Sumbal Saba
TL;DR
This paper presents a new electrochemical method to efficiently synthesize 3-selenylated chromone compounds under mild conditions.
Contribution
A novel electrosynthesis method for 3-selenylated chromones via a domino C(sp2)-H bond selenylation/annulation process.
Findings
The method operates under mild conditions with good functional group tolerance.
The reaction is scalable and has a wide substrate scope.
The reaction likely proceeds via a cation pathway based on preliminary experiments.
Abstract
Herein, we disclose a highly efficient pathway toward 3-selenylated chromone derivatives via electrosynthesis domino C(sp2)-H bond selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, a wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amenable to scaling up the reaction. Additionally, the preliminary experiments revealed that this reaction probably proceeded via a cation pathway instead of a radical pathway.
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Taxonomy
TopicsRadical Photochemical Reactions · Sulfur-Based Synthesis Techniques · Catalytic C–H Functionalization Methods