Anomeric amides have been known and extensively studied for over 40 years. This work points to a new use for halogenated variants (Cl and Br) of such structures that can take advantage of embedded hybridization/strain that is restored/released when those halogen atoms depart. The resulting reagents demonstrate high reactivity, regio-, and chemoselectivity in challenging electrophilic aromatic halogenations when even the most powerful conditions currently known are low yielding or unfeasible. The safety profile of these structures was studied and numerous gram-scale batch reactions and a decagram flow reaction in mock process setting were demonstrated. Preliminary findings suggest these reagents can have utility in other halogenation reactions as well. Computational studies support the initial hypothesis and may serve as a foundation for the development of other versatile reagents and uses of anomeric amide scaffolds in synthesis. NBS, BPO: 28% NBS, AcOH: 36% (1) ketone α-bromination