Cathode and medium effects on the electroreductive glucosidation of phenols

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