A reagent for heteroatom borylation, including iron mediated reductive deoxygenation of nitrate yielding a dinitrosyl complex.

4,4'-Bipyridyl is shown to be a catalyst for transfer of pinacolboryl groups from (Bpin)2 to nitrogen heterocycles and to Me3SiN3. Using stoichiometric (Bpin)2(pyrazine) or (Bpin)2(bipyridine) in an analogous manner, an aromatic nitro group is deoxygenated and subsequently borylated, and four-fold deoxygenation of (DIM)Fe(NO3)2(MeCN) to yield the dinitrosyl complex (DIM)Fe(NO)2 is facile. The co-product O(Bpin)2 is the quantitative fate of the removed oxo groups. With borylation of both nitrogen heterocycles and doubly deoxygenating two nitrates coordinated to a single metal center, broad spectrum methodology is demonstrated.