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
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
› Author Affiliations
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.

Supporting Information



Publication History

Received: 13 December 2022

Accepted after revision: 20 February 2023

Accepted Manuscript online:
20 February 2023

Article published online:
22 March 2023

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