Electrocatalytic Aziridination of Alkenes in an Undivided Cell Mediated By Iodide

Wednesday, 27 May 2015: 14:40
PDR 5 (Hilton Chicago)
C. Zeng (College of Life Science & Bioengineering) and J. Chen (Beijing University of Technology)

Efficient synthesis of aziridines is of significant importance due to their various biological activities and potential application in organic synthesis. The most popular approach to construct aziridine ring is the reaction of alkene with nitrene or its precursors. To this end, a variety of chemical protocols have been developed using chloramine-T or N-aminoheterocycles as nitrogen source in the presence of chemical oxidant. On the other hand, an electrochemical process for aziridination of alkenes with PhthNH2 was also reported in a divided cell at a controlled potential using Pt as a working electrode.

Based on our previous work, we hypothesized that the electrochemically generated oxidative state of halide species may also apply to the catalytic aziridination reaction of alkene and PhthNH2. Herein, we reported an electrochemical approach for the efficient catalytic aziridination of alkenes using iodine ion as a redox catalyst. The process is conveniently carried out at constant current in an undivided cell.