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Carbon-nitrogen bonds (C-N) bonds are ubiquitous in both natural and unnatural small molecules, especially those with potential bioactivity. This work is focused on the development of new methods for C-N bond formation, specifically aziridines, via nitrene intermediates through metal-mediated visible-light photocatalysis. Iridium bypyridyl complexes have been shown to mediate this generation of nitrenes from stabilized azides (azidoformates), which can then be transferred to alkenes to afford aziridines. To better understand this process, we have prepared alternatives to the azidoformate precursor: N-tosyloxy carbamates and N-protected aminopyridinium salts. A study of the nature of the nitrene precursor, metal catalyst, reaction conditions and rate of product formation is explored in aziridination under visible light photocatalysis.
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This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.
Wu, Victoria Emily, "Nitrene Generation Via Visible-light Photocatalysis: Aziridination From Electrophilic Amine Sources" (2019). Senior Projects Fall 2019. 5.