Carbon-nitrogen (C-N) bonds are ever-present in both natural and unnatural small molecules, especially those with potential bioactivity. Our research group has been interested in developing new synthetic methods to create two C-N bonds, simultaneously, to afford substituted aziridine products. This work is focuses on the design of a visible light-driven process where a metal photocatalyst alongside blue LED light promotes the direct aziridination of substituted alkenes (C=C) using N-aminopyridinium ylides as the nitrogen source. Reports in the literature have recently proven that nitrenes can be generated from azidoformates using visible light catalysis and will form aziridines in the presence of olefins. To better understand this process and how it relates to other electrophilic amines, we are currently investigating ylides derived from N-protected aminopyridinium salts. The effects on stoichiometry, electronics of the nitrogen source, and the identity of the alkene reaction partner are observed through NMR studies and reported here.

Photocatalytic C-N bond formation: Mechanism and scope of alkene aziridination with N-aminopyridinium ylides

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

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