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Carbon-nitrogen bonds are pervasive in a wide-ranging assortment of small molecules. Perhaps the most atom-economical method for the creation of C-N bonds is the nitrene insertion reaction. Iridium bypyridyl complexes have been shown to mediate visible light nitrene transfer to alkenes to afford aziridines. This study focuses on the energy transfer or photosensitization from Ir(III) and Pt(II) transition metal complexes to stabilized organic azides. Our work shows that the rate of the this aziridination is governed by the type of photocatalyst and azide employed. For example, the use of [Ir(ppy)2(dtbbpy)]PF6with TrocN3results in a 94% conversion of styrene to the aziridine product, however no product was observed using [Ir(Fppy)2(dtbbpy)]PF6. A study of the effects of catalyst structure, physical properties, and stability is presented along with the differences in reactivity of two azidoformate nitrene precursors in aziridine formation is explored.
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Anyanwu, Chibuzo Praise, "Visible Light Aziridination via Photosensitization of Stabilized Nitrenes: an Investigation on Iridium and Platinum Photocatalysts" (2018). Senior Projects Spring 2018. 22.