Aziridination of a Single Carbon Atom in Alkenes via Energy Transfer Catalysis

Abstract

ABSTRACT Traditional alkene aziridination relies on the alkene's reaction with a (formal) nitrene species, whereby the alkene provides both carbon atoms for the formed heterocycle. In contrast to this paradigm, we herein report a divergent manifold consisting of intermolecular aziridination at a single alkene site with concomitant functionalization of the second alkene site. This process unlocks alternative chemical space from alkenes through energy transfer‐catalyzed difunctionalization of alkenyl boronates and silanes toward spring‐loaded imine intermediates and their subsequent facile conversion to an aziridine involving a 1,2‐aza‐(bora‐)Brook rearrangement. The use of visible light and the absence of metals, additional bases, and external heating allow for mild reaction conditions that furnish unprotected and highly substituted aziridines.