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Continuous flow technology was exploited for the effective generation of nitrile imines via photolysis of substituted aryl tetrazoles. The resulting photo-click process was used to rapidly afford advanced nitrogen-rich scaffolds upon the subsequent trapping of the reactive dipole with alkenes, alkynes, and benzylic amines. Crucially, differential reactivity between ether and amine tethers was uncovered through this approach, thereby providing facile and scalable access to underexplored medicinally relevant heterocyclic entities.