Electrochemical Silver-Catalyzed [2 + 2 + 1] Decarboxylation of N-Aryl Glycines with Azobenzenes Access to 1,2,4-Triazolidines

Refraining from metal deposition through cathodic reduction poses a significant challenge in transition-metal-catalyzed electrosynthesis under direct current (DC) conditions. Herein, an electrochemical silver-catalyzed [2 + 2 + 1] decarboxylation of N -aryl glycines with azobenzenes access to 1,2,4-triazolidines has been disclosed. This electrochemical silver-catalyzed decarboxylation protocol demonstrates exceptional efficiency and circumvents any cathodic metal deposition in an undivided cell. Mechanistic studies have demonstrated that the inclusion of N -aryl glycines and pyridines in this electrochemical/Ag II -mediated decarboxylation protocol plays a crucial role in preventing the formation of silver mirrors.