Electrosynthesis of dimeric butenolides by C-C-homocoupling in the oxidation of 2,4-diarylfurans under aqueous conditions

Autor: Belen Batanero, Noemi Salardon, Elena Prieto-Garcés, Lorena Herrera, Soufyane Er-Ryhy, M. Teresa Quirós, Natalia Gómez-Casanova, Irene Heredero-Bermejo, José Luis Copa-Patiño
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: iScience, Vol 27, Iss 9, Pp 110765- (2024)
Druh dokumentu: article
ISSN: 2589-0042
DOI: 10.1016/j.isci.2024.110765
Popis: Summary: Fast and efficient galvanostatic conversion of 2,4-diarylfurans into dimeric furan-2(5H)-ones is now possible in one pot and good yields at room temperature in sustainable aqueous organic solvent. Recent applications of these highly desired structures demand our attention since they are a versatile alternative to acrylates in polymerization to achieve green materials. The reaction mechanism proposal, supported by density functional theory (DFT) theoretical calculations, involves furanoxy radicals, detected by electron paramagnetic resonance (EPR), as the last intermediate before a homocoupling step that affords butenolides. The process can be successfully extended to an array of electron-donating and electron-withdrawing substituents on the aromatic ring. The proposed pathways to explain the formation of the products are rationalized and discussed. A concomitant oxidation of water to hydroxyl radicals is not discarded, particularly with electron-withdrawing substituents at the aromatic ring. In addition, the biological activity as biocides of the obtained compounds was tested, and they showed promising activity against Staphylococcus aureus.
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