Cathode and medium effects on the electroreductive glucosidation of phenols

Abstract

The electroreductive pathway to phenol glucosidation, recently introduced by our research group, is analysed here in detail for both mechanism elucidation and choice of operating conditions. Preparative electrosyntheses were carried out on model substrates, varying either the cathode material, the supporting electrolyte, and/or the potential/current electrolysis conditions, to study their effects on the glucosidation yields and stereochemistry. Special care was devoted to the analysis of the reaction mixtures, leading to the identification and characterisation of several new products.