Electrochemical Aziridination of Internal Alkenes with Primary Amines

Summary Aziridines are useful synthetic building blocks, widely employed for the preparation of various nitrogen-containing derivatives. As current methods require use prefunctionalized amines, development a strategy toward aziridines that can establish union alkenes and amines would be great value. Herein, we report an electrochemical approach, which realizes this concept via oxidative coupling between primary alkylamines. The reaction is carried out in flow reactor leading to short reaction/residence times (5 min), high yields, broad scope. At cathode, hydrogen generated, used second reduce aziridine, yielding corresponding hydroaminated product. Mechanistic investigations DFT calculations revealed alkene first anodically oxidized subsequently reacted with amine partner.