Generally, the position-selectivity for halogenation was in accord with what one would normally predict , although 13 out of the 41 examples favored different sites (see SI for predicted halogenation sites). In some cases, such as 20, 44, and 46, the halogenation regioselectivity using 6/7 can be dramatically improved relative to known protocols. Anomeric amide halogenating reagents also exhibit exquisite chemoselectivity relative to the state-of-the-art. For instance, attempted chlorination of celecoxib (26) using Palau'chlor furnished only sulfonamide N-chlorination rather than the desired chloropyrazole product which was exclusively observed using reagent 6 (93% yield on gram-scale). When the simple indazole building block 17 was exposed to Palau'chlor (1.2 equiv, rt, 24 h), ca. 50% conversion to the N-Cl adduct was observed. Subsequent heating at 70 °C for 20 h delivered 47% of 17-Cl, 24% recovered 17, and 27% of dichlorinated 17 (NMR yield). In contrast, using reagent 6 (1.2 equiv, rt, 24 h), a 91% isolated yield of the desired product 17-Cl was observed. In the case of pesticide 42, reagent 7 delivered 42-Br in 47% isolated yield whereas treatment with NBS/AcOH led to 6% desired product (NMR yield) along with a variety of unidentified products.