Pd, Ni Cu, or hv delivers mixtures of nitrate esters. The main challenge for the present study, as outlined in Table , was to identify an •NO2 donor reagent that is capable of reacting at N rather than O without altering the oxidation state at N. Existing precedent using MHAT chemistry in concert with arylnitro compounds (17) illustrates this challenge with Fe-H based methods from this lab and Studer. In the former case, the reductive conditions proceed via Path B (presumably through intermediates 20 and 21) but exhaustive reduction delivers amine product 22 whereas the latter case reacts exclusively via Path A (via 18) to deliver tertiary alcohol 19.