Direct oxidation of alcohols or amines enables access to carbonyl or imine compounds, such as aldehydes or aldimines, which may undergo further follow-up reactivity. Many textbook oxidation processes are unsuitable when adapted for practical synthesis; heavy metal oxidants may generate toxic wastes, while many organic oxidants are expensive and require stoichiometric amounts, which decrease atom efficiency by introducing large quantities of unused products. High selectivity for oxidation can also be challenging, as substrate over-oxidation is commonly observed with harsh oxidants. Thus, careful catalyst design that maximizes selectivity and minimizes waste is among key attributes of an ideal oxidation catalyst. We have been targeting pincer-ligated NNN-Ru(II) complexes that function as efficient dehydrogenation catalysts with high chemoselectivity. This presentation will elaborate on efforts toward the oxidation of carbon-heteroatom bonds, with liberation of dihydrogen under moderate conditions. Progress toward achieving high chemoselectivity and mechanistic insight into dehydrogenation processes will be described.

Selective dehydrogenative reactivity catalyzed by a pincer-ligated Ru(II) hydride

246th National Meeting (2013)

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