Exploiting Imine Photochemistry for Masked N-Centered Radical Reactivity

Abstract

This report details the development of amasked Ncentered radical strategy that harvests the energy of light to drive the conversion of cyclopropylimines to 1-aminonorbornanes.T his process employs the N-centered radical character of ap hotoexcited imine to facilitate the homolytic fragmentation of the cyclopropane ring and the subsequent radical cyclization sequence that forms two new C À Cb onds en route to the norbornane core.A chieving bond-forming reactivity as af unction of the N-centered radical character of an excited state Schiff base is unique,r equiring only violet light in this instance.T his methodology operates in continuous flow, enhancing the potential to translate beyond the academic sector.T he operational simplicity of this photochemical process and the structural noveltyo ft he (hetero)aryl-fused 1aminonorbornane products are anticipated to provide av aluable addition to discovery efforts in pharmaceutical and agrochemical industries.