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.
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Diana Baumrind (1970) studied this question.
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