Synthesis 2023; 55(18): 2985-2992
paper
Special Issue Electrochemical Organic Synthesis
Electrosynthesis of Flavanones via oxa-Michael Addition Using Sacrificial Electrodes
William A. B. Santos
a
Department of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil
b
Department of Chemistry, Federal University of Santa Catarina (UFSC), Florianópolis – SC, 88040-900, Brazil
,
Pedro P. de Castro
c
Department of Chemistry, Federal University of São Carlos (UFSCar), São Carlos – SP, 13565-905, Brazil
,
Fernando R. Xavier
a
Department of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil
,
Antonio L. Braga
b
Department of Chemistry, Federal University of Santa Catarina (UFSC), Florianópolis – SC, 88040-900, Brazil
,
Guilherme M. Martins∗
c
Department of Chemistry, Federal University of São Carlos (UFSCar), São Carlos – SP, 13565-905, Brazil
,
a
Department of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil
› Institutsangaben The authors would like to thank the FAPESP (grant numbers: 2022/00074-3 (G. M. M.), and 2021/13924-2 (P. P. C.), FAPESC (grant number: 2021TR964), Capes (001) and INCT-Catálise-FAPESC.
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
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-2038-9146.
Supporting Information
Publikationsverlauf
Eingereicht: 13. Dezember 2022
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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