Cathode and medium effects on the electroreductive glucosidation of phenols

The electroreductive pathway to phenol glucosidation, recently introduced by the authors' research group, is analyzed 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 stereochem. Special care was devoted to the anal. of the reaction mixts., leading to the identification and characterization of several new products.