Dihydrolevoglucosenone (Cyrene™), a new possibility of an environmentally compatible solvent in synthetic organic electrochemistry.

Faraday Discuss

Centro Conjunto de Investigación en Química Sustentable UNAEM-UNAM, Toluca, 50200, Estado de México, Mexico.

Published: October 2023

Dihydrolevoglucosenone (DLG or Cyrene™) solvent is a green dipolar solvent produced from cellulose waste. Different studies have demonstrated that it can successfully replace dipolar solvents, such as ,-dimethylformamide (DMF), ,-dimethylacetamide (DMA) and -methylpyrrolidinone (NMP), in a variety of chemical reactions. In this paper, the first application of DLG in organic electrosynthesis is described, with results of its use in the electrochemical reduction of benzophenone derivatives ( = -1.75 V Ag/AgCl), as a greener alternative to other dipolar solvents with environmental concerns. Conductivity measurements show that the solvent presents conductivity and viscosity limitations that can be overcome by using EtOH as a cosolvent. The DLG/EtOH mixture resulted in a convenient solvent to carry out galvanostatic electroreductions of starting materials that exhibit high potential value. Furthermore, the reaction pathway (1e or 2e) was found to be dependent on the supporting electrolyte used; TBABF favored 2e reduction to the corresponding alcohol (52-85%), whereas LiClO promoted C-C pinacolic coupling (47-70%).

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http://dx.doi.org/10.1039/d3fd00064hDOI Listing

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