The direct synthesis of aziridines from alkenes and nitrene sources (C<sub>2</sub>+N<sub>1</sub>) with the correct functionality on the nitrogen atom has remained an elusive goal in synthetic chemistry.  Our group is expanding the scope of catalytic aziridination to include electron donating aryl azides and aliphatic alkenes through the use of novel tetracarbene iron catalysts.  To improve the design of next generation catalysts, a detailed understanding of the mechanism and intermediates is vital.  The reaction of organic azides with tetracarbene iron(II) complexes leads to high valent iron(IV) intermediates, including metallotetrazenes.  Both first and second generation tetracarbene ligands support these iron(IV) complexes.  The structural and spectroscopic properties of these unusual iron(IV) complexes will be discussed as well as their group transfer reactions.

Tetracarbene iron(IV) intermediates for catalytic aziridination

249th National Meeting (2015)

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