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report details the development of a masked N-centered
radical strategy that harvests the chemical potential of violet light to drive
the conversion of cyclopropylimines to 1-aminonorbornanes. This process is
initiated by the nitrogen-centered radical character of a photoexcited imine,
facilitating the homolytic fragmentation of the cyclopropane ring followed by a
radical cyclization sequence that forms two new C–C bonds en route to the
norbornane core. Employing the excited state diyl of a Schiff base as a masked N‑centered radical is a unique mode of
reactivity, the utility of which is amplified by the bathochromic shift into
the visible spectrum imparted by the 4-nitrobenzimine. In addition to the
intramolecular reactivity that generates 1‑aminonorbornanes, intermolecular
formal [3+2] cycloadditions are also amenable to this strategy. This
photochemical methodology operates in continuous flow, enhancing the potential
to translate this approach beyond the academic sector.