Arguably the most atom-economical method for the creation of carbon-nitrogen bonds is nitrene insertion.  Despite challenges associated with control and selectivity in nitrene chemistry, progress within this research area remains robust. This work explores in situ oxidation methods of nitrene formation from carbamates, followed by a study in selectivity in alkene aziridination. Preliminary results show that electronic control of the alkene and choice of a hypervalent iodine oxidant are important in the spectroscopic observation and subsequent isolation of aziridine products. Substrate design, the scope of reactivity, and an optimization of reaction conditions is reported.

C-N bond formation: Oxidation and metal-mediated transfer of carbamate-derived nitrenes for the intramolecular aziridination of alkenes

256th National Meeting (2018)

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