Electrochemical Ring Opening and [3 + 2] Cycloaddition of Aziridines: Access to 1,2-Bifunctionalized Products and Imidazolines

Herein, we report an electricity-driven activation of aziridine via direct anodic oxidation to give N -heterocycles and 1,2-bifunctionalized products by excluding any oxidant/reductant or metal catalyst. Many structurally modified aziridines were employed in the presence of different nitriles. A large variety of nucleophiles were screened to furnish chemoselectively O-alkylated and C-alkylated products. Late-stage derivatization of aziridine with natural and medicinally active compounds has also been done. Remarkably, our strategy was found to be a greener, sustainable, and atom-economical approach ( E -factor = ca. 0.8). Azetidine was also found to be compatible with our protocol and generated six-membered N -heterocycles. The detailed mechanistic study highlighted that the reaction is driven via the generation of an aziridine radical cation followed by the S N 2 nucleophilic attack.