Organic Chemistry

Electrochemical Aziridination of Internal Alkenes with Primary Amines

Abstract

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

Content

Thumbnail image of Aziridine_ ACS-V12.pdf

Supplementary material

Thumbnail image of Aziridine-SI-V9.pdf
Aziridine-SI-V9