Batanero Belen, Salardon Noemi, Prieto-Garcés Elena, Herrera Lorena, Er-Ryhy Soufyane, Quirós M Teresa, Gómez-Casanova Natalia, Heredero-Bermejo Irene, Copa-Patiño José Luis
University of Alcala, Department of Organic Chemistry and Inorganic Chemistry and Institute of Chemical Research Andrés M. del Rio, 28805 Alcala de Henares, Madrid, Spain.
University of Alcala, Department of Biomedicine and Biotechnology, 28805 Alcalá de Henares, Spain.
iScience. 2024 Aug 22;27(9):110765. doi: 10.1016/j.isci.2024.110765. eCollection 2024 Sep 20.
Fast and efficient galvanostatic conversion of 2,4-diarylfurans into dimeric furan-2(5)-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 .
现在可以在可持续的水有机溶剂中，于室温下通过一锅法以良好的产率将2,4-二芳基呋喃快速高效地恒电流转化为二聚呋喃-2(5)-酮。这些备受期待的结构的最新应用值得我们关注，因为它们是聚合反应中丙烯酸酯的通用替代品，可用于制备绿色材料。由密度泛函理论（DFT）理论计算支持的反应机理推测表明，电子顺磁共振（EPR）检测到的呋喃氧基自由基是生成丁烯内酯的均偶联步骤之前的最后中间体。该过程可以成功扩展到芳环上一系列供电子和吸电子取代基的情况。对所提出的解释产物形成的途径进行了合理化分析和讨论。不排除水同时氧化为羟基自由基的情况，特别是在芳环上有吸电子取代基时。此外，还测试了所得化合物作为杀生物剂的生物活性，它们对……显示出有前景的活性。
