To explore the scope of the transformation, the optimized conditions were applied to a series of functionalized starting materials. The reaction was performed using either 0.5 or 1 equivalent of DIPEA (indicated as conditions A and B, respectively, in Figure ) depending on the conversion of starting materials. In addition to electron-deficient benzamide derivatives which gave good yields with both sets of conditions (2a-c, up to 97% yield), it was gratifying to observe that the protocol was compatible with a range of medicinally relevant heterocycles, including quinolines, pyrazines and pyridines (2d-f, up to 89%). Cinnamamides were then explored to evaluate the compatibility of the method with α,β-unsaturated carbonyl derivatives (2g-j, up to 82% yield). It is pertinent to note that regioisomers 2h and 2i showed slight differences in reactivity which is likely a manifestation of two 1,3-allylic strain scenarios subtly attenuating the redox potential of the substrate. Another example of the influence of 1,3-allylic strain on the redox potential is the cinnamamide 1h and its stereoisomer 1j, which was generated by photocatalytic isomerization. They showed different behavior under the reaction conditions, however the alkene geometry is preserved fully in both cases (products 2i and 2j). Cognizant of the importance of diene fragments in complex natural product synthesis, and the sensitivity of these structural modules to established N-O bond cleavage protocols (see Figure ), secondary amides 2k, 2l and 2m were prepared in up to 62% yield. The presence of a C(sp 2 )-B until provides a convenient handle for subsequent drown-stream manipulation. Replacing the N-Me by N-pentenyl afforded the product 2n in 59% yield: the pyrroldine-based product that would arise from amidyl radical formation and subsequent 5exo-trig cyclization was not observed thereby indicating mechanistic distinction of this process compared redox auxiliary approaches (vide infra). In a final twist of fate, a model hydroxylamide (N-OH), when exposed to these conditions, was smoothly converted to product 2a and it was possible to generate the primary amide 2o. In general, the method is limited to electron-poor substrates, with electron neutral or -rich Weinreb amides giving only traces of the desired product and the starting material was recovered. (89 )