Aromatic amines are a ubiquitous, albeit highly reactive functional group that frequently requires protection to prevent undesired reactivity. Although numerous protecting groups exist for aromatic amines, a more efficient and economical strategy often involves the reduction of nitro groups to unmask the amine late in the synthesis. Nevertheless, whilst the nitro group is robust enough to withstand numerous reaction conditions, the reduction can be particularly challenging with respect to chemoselectivity. Hence, the development of a mild, selective and catalytic reduction of an aromatic nitro group to the corresponding aniline constitutes a fundamentally important transformation for target-directed synthesis. This presentation will describe the development of a new catalytic approach to the chemoselective hydrogenation of aromatic nitro groups employing a novel heterogeneous nickel catalyst that demonstrates excellent chemoselectivity for an array of highly substituted aromatic substrates. In addition, we will present the unique characteristics of the nickel catalyst using scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS) to provide insight into the catalytic activity.

Chemoselective nickel-catalyzed hydrogenation: Synthesis of highly substituted aromatic amines

2019 Fall National Meeting

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