Carbon-nitrogen (C-N) bonds are ubiquitous in both natural and unnatural small molecules, especially those with potent bioactivity. This work is focused on the development of new methods for C-N bond formation via nitrene intermediates through metal-mediated 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 aminopyridium salts. A study of the nature of the nitrene precursor, metal catalyst, reaction conditions, and rate of product formation is explored in aziridine formation under visible light photocatalysis.

Nitrene generation via visible-light photocatalysis: Aziridination from electrophilic amine sources

2019 Fall National Meeting

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