(Cyclopentadienone)iron carbonyl compounds were first prepared in the late 1950s, but it was not until 2007 that their catalytic activities were explored. Structurally similar to Shvo’s bridging diruthenium hydride, they catalyze alcohol oxidations, carbonyl and imine reductions, and a wide variety of borrowing hydrogen processes through a transfer hydrogenation mechanism. We are interested in increasing the safety and sustainability of alcohol oxidations, and this class of catalysts was appealing because they use simple carbonyl compounds as terminal oxidants (i.e., hydrogen acceptors). We and others showed that acetone is an effective solvent/hydrogen acceptor when electron-rich alcohols are being oxidized, but its low oxidation potential combined with the equilibrium-driven nature of the reaction limited the scope of alcohols that could be used. We recently discovered that cellulosic biomass-derived furfural is an effective hydrogen acceptor when used in (cyclopentadienone)iron-catalyzed alcohol oxidations, and its high oxidation potential increased the scope of reactive alcohols. Details about our studies, including optimization of the reaction work-up and substrate scope, will be presented.

Sustainable, iron-catalyzed alcohol oxidations with a biomass-derived terminal oxidant

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