Volume 247, 2023

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

Abstract

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 N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA) and N-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 (ca. E = −1.75 V vs. 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; TBABF4 favored 2e reduction to the corresponding alcohol (52–85%), whereas LiClO4 promoted C–C pinacolic coupling (47–70%).

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

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Article information

Article type
Paper
Submitted
11 мар. 2023
Accepted
23 мар. 2023
First published
01 апр. 2023

Faraday Discuss., 2023,247, 182-194

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

J. M. Ramos-Villaseñor, J. Sotelo-Gil, S. E. Rodil and B. A. Frontana-Uribe, Faraday Discuss., 2023, 247, 182 DOI: 10.1039/D3FD00064H

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