Ricerc@Sapienza

The benzoin condensation starting from benzaldehyde and the subsequent benzoin amidation to benzamide can be efficiently carried out under very mild conditions in an electrolysis cell. Among the advantages of using electrochemistry to generate our active reagents, the use of the easily dosed and non pollutant electron, instead of stoichiometric amounts of redox reagents or bases, usually renders the electrochemical methodology “greener” than classical organic reactions. Benzoin is obtained in good yield (85 %) carrying out the reaction in the room temperature ionic liquid BMIm-BF4.

Amide function is very important in both organic and medicinal chemistry. Benzamides can be obtained
in good to high yields by reaction of benzoin, primary or secondary amines, molecular oxygen and
electrogenerated superoxide anion (obtained with galvanostatic method). The advantage of using
electrogenerated superoxide anion is related to its counterion, the tetraethylammonium cation, which is
not tightly bound to the anion and thus renders superoxide highly reactive also in the absence of