Rapid ether and alcohol C-O bond hydrogenolysis catalyzed by tandem high-valent metal triflate + supported Pd catalysts.

Abstract

The thermodynamically leveraged conversion of ethers and alcohols to saturated hydrocarbons is achieved efficiently with low loadings of homogeneous M(OTf)n + heterogeneous Pd tandem catalysts (M = transition metal; OTf = triflate; n = 4). For example, Hf(OTf)4 mediates rapid endothermic ether ⇌ alcohol and alcohol ⇌ alkene equilibria, while Pd/C catalyzes the subsequent, exothermic alkene hydrogenation. The relative C-O cleavage rates scale as 3° > 2° > 1°. The reaction scope extends to efficient conversion of biomass-derived ethers, such as THF derivatives, to the corresponding alkanes.

DOI: 10.1021/ja411546r

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Cite this paper

@article{Li2014RapidEA, title={Rapid ether and alcohol C-O bond hydrogenolysis catalyzed by tandem high-valent metal triflate + supported Pd catalysts.}, author={Zhi Li and Rajeev S. Assary and Abdurrahman C. Atesin and Larry A. Curtiss and Tobin J Marks}, journal={Journal of the American Chemical Society}, year={2014}, volume={136 1}, pages={104-7} }