Electrosynthesis of Flavanones via oxa-Michael Addition Using Sacrificial Electrodes

William A. B. Santos; Pedro P. de Castro; Fernando R. Xavier; Antonio L. Braga; Guilherme M. Martins; Samuel R. Mendes

doi:10.1055/a-2038-9146

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(18): 2985-2992
DOI: 10.1055/a-2038-9146

paper

Special Issue Electrochemical Organic Synthesis

Electrosynthesis of Flavanones via oxa-Michael Addition Using Sacrificial Electrodes

William A. B. Santos

^aDepartment of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil

^bDepartment of Chemistry, Federal University of Santa Catarina (UFSC), Florianópolis – SC, 88040-900, Brazil

,

Pedro P. de Castro

^cDepartment of Chemistry, Federal University of São Carlos (UFSCar), São Carlos – SP, 13565-905, Brazil

,

Fernando R. Xavier

^aDepartment of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil

,

Antonio L. Braga

^bDepartment of Chemistry, Federal University of Santa Catarina (UFSC), Florianópolis – SC, 88040-900, Brazil

,

Guilherme M. Martins∗

^cDepartment of Chemistry, Federal University of São Carlos (UFSCar), São Carlos – SP, 13565-905, Brazil

,

Samuel R. Mendes ∗

^aDepartment of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil

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Abstract

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Abstract

An electrochemical synthesis of flavanones via oxa-Michael addition using silver electrode as a sacrifice is reported. This electrosynthetic system showed good yields, broad substrate scope, and good functional group tolerance. Additionally, the method proved to be applicable on a gram-scale. Several studies were carried out to elucidate the reaction mechanism, such as control reactions, cyclic voltammetry, and theoretical studies, allowing the proposal of a plausible pathway for this transformation.

Key words

electrosynthesis - sacrificial electrodes - silver - flavonoids - cyclization

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