Generally speaking, chlorine and bromine atoms are amongst the only functional groups that can be viewed as both facile precursors (gateways) to other functionality (through cross-coupling ) and potentially useful for their inclusion in a final drug substance . Indeed, numerous FDA approved drugs contain these halogen atoms, and their introduction can often have a documented "magical" effect on desired properties . For instance (Figure ), the potency of lead structures 1 5 and 2 6 could be improved by several orders of magnitude by the simple installation of chlorine and bromine atoms, respectively. Electrophilic aromatic halogenation 7 is arguably the earliest example of industrial practitioners embracing the now wildly popular strategies of "late-stage functionalization" and C-H functionalization . In fact, recent reviews point to electrophilic halogenation as being one of the reaction classes most prized by medicinal chemists . Numerous elegant approaches relying on C-H activation or indirect halogenation via intermediate species have emerged to provide alternative tactics to access halogenated arenes. That said, there are numerous contexts for which the available reaction and reagent toolkit are insufficient to satisfy demand such as the halogenation of the simple triazole found in vericonazole (3, Figure ). Historical approaches to increase the power of electrophilic halogenation are summarized in Figure and generally rely either on the invention of new reagents or by activating known reagents with additives . The majority of electrophilic halogenation reagents are based on stable N-X bonds wherein the flanking substituents on nitrogen include various electron withdrawing groups. Anomeric amides (Figure ), first introduced by Glover and widely studied in the 1980's have historically been utilized as nitrenium ion precursors via nucleophilic attack at nitrogen . In contrast, there have been no investigations we are aware of wherein these unusual species have been harnessed to activate a halogen atom. The premise of this study was that enhanced reactivity might result from the use of reagents based on an anomeric amide by virtue of a spring-loaded driving force to rehybridize following halogenation from a sp 3 to sp 2 nitrogen center. In this disclosure (Figure ), a new class of powerful electrophilic reagents based on anomeric amides is presented. Through extensive benchmarking with state-of-the-art protocols, it is shown that such reagents are extremely useful for achieving scalable (in batch and flow settings) and efficient arenes chlorination and bromination at both an early and late stage. Their halogenating power is not limited to arenes as advantages are observed with other reaction manifolds; a computational study supports the defining role of the anomeric amide motif. Very little precedent exists for the synthesis of anomeric amide halogenating agents such as 6 and 7 (Figure ). Studies commenced from the known compound 5, constructed using a modified procedure that avoids chromatographic purification on decagram scale (see SI). In order to access chlorinating reagent 6, t BuOCl was employed as it proceeded in quantitative yield and simplified subsequent purification (filtration). Related systems had been chlorinated before using TCCA which was deliberately avoided for practical reasons. In the case of brominating reagent 7, a AgOAc-mediated procedure using Br2 was employed followed by recrystallization. Although reagents 6 and 7 are bench-stable solids prepared through scalable and practical procedures, they were stored below 0°C to minimize gradual decomposition.