Progress Toward the Photo-Assisted Reductive Cross-Coupling of Alkyl Aziridines

Abstract

Progress toward the nickel-catalyzed, photo-assisted reductive cross-coupling of styrenyl, acrylate-derived, and particularly, alkyl aziridines is reported. This method integrates a photocatalyst and homogeneous terminal reductant with a nickel catalyst and ligand to effect the cross-coupling of alkyl aziridines, yielding exclusively linear products (C-N bond cleavage occur at the least substituted position). The optimization of this versatile reaction on two different scales is detailed. Moreover, preliminary but broad aziridine and aryl iodide substrate scopes are discussed. Experiments conducted on this system have elucidated its strengths and limitations, and have informed continuing scope studies as well as plans for mechanistic investigation.