R-021

María Belén Batanero Hernan

belen.batanero@uah.es

Noemi Salardón, M. Teresa Quirós, Irene Heredero-Bermejo, Natalia Gómez-Casanova, Jose Luis Copa-Patiño

Universidad de Alcalá, Spain

Electrochemical Oxidation of  2,4-Diarylfurans to Dimeric Butenolides

Furan-2(5H)-ones (butenolide core moieties) are important building-blocks in organic chemistry that are present in many natural products and show potent bioactivity. These molecules have been evaluated for their use as anti-inflammatories, in cancer therapeutics or as antifungal agents. Particularly, 5-Aryl-gamma-lactones are considered a kind of “chemical defense” as they have been collected from microorganisms grown in harsh environments.

Dimeric 3,5-diarylfuran-2(5H)-ones have been now easily prepared in good yield and a one-pot electrochemical reactor from their parent 2,4-diarylfurans via constant current anodic oxidation in acetonitrile/water as Solvent-Supporting-Electrolyte system (SSE).

The experimental reaction parameters were optimized by changing the electrochemical cell, the solvent/water content, the electrolyte nature or the anode material. The transformation is rationalized as a C-C homocoupling reaction that has been extended to a scope of substrates. Plausible mechanism pathways are presented and discussed based on DFT calculations, cyclic voltammetry and according to control experiments.