Synthesis of β‑Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides

A photoassisted Ni-catalyzed
reductive cross-coupling between tosyl-protected
alkyl aziridines and commercially available (hetero)­aryl iodides is
reported. This mild and modular method proceeds in the absence of
stoichiometric heterogeneous reductants and uses an inexpensive organic
photocatalyst to access medicinally valuable β-phenethylamine
derivatives. Unprecedented reactivity was achieved with the activation
of cyclic aziridines. Mechanistic studies suggest that the regioselectivity
and reactivity observed under these conditions are a result of nucleophilic
iodide ring opening of the aziridine to generate an iodoamine as the
active electrophile. This strategy also enables cross-coupling with
Boc-protected aziridines.