The ability to cleanly halogenate at the end of a synthetic route could have benefits in a medicinal chemistry program. For example, structures 27 38 , , and Preliminary explorations also point to the enhanced reactivity of anomeric amide reagents in settings other than electrophilic aromatic substitution (Figure ). For instance, in the a-bromination of (hetero)aromatic methyl ketones (47-49), superior selectivity for mono-bromination is observed across the board. Similarly, the acidic methylene group of cyclic N-sulfonylimine 50 could be efficiently brominated with a superior yield (83%) compared with known procedure (24%) using Py-HBr3 . An improved yield was also observed in allylic bromination of (R)-carvone (51) relative to standard conditions . Finally, enol acetate 52 (prasugrel) could be chlorinated in nearly quantitative yield.