The direct synthesis of aziridines from alkenes and nitrene sources with the correct functionality on the nitrogen atom has remained an elusive goal in synthetic chemistry.  A simpler and more atom economical catalytic C2+N1 aziridination would accomplish this goal by utilizing an alkene and an aryl or alkyl azide as the nitrene source.  Our group is expanding the scope of catalytic aziridination to include electron donating aryl azides and aliphatic alkenes through the use of novel tetracarbene catalysts on group 8 metals.  We have synthesized a new ligand platform based on small-ringed (16 or 18 atoms) macrocyclic tetraimidazoliums as tetracarbene precursors.  These tetraimidazoliums form monomeric tetracarbene complexes on iron and ruthenium with two open sites at the metal.  The structural and spectroscopic properties of these complexes will be discussed as well as the results of catalytic aziridination reactions with a variety of alkenes and organic azides.

Catalytic aziridination using macrocyclic tetracarbene complexes of iron and ruthenium

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.