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

Journal of the American Chemical Society
Zhi LiTobin J Marks

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.

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Citations

Apr 15, 2016·Accounts of Chemical Research·Tracy L LohrTobin J Marks
May 21, 2015·Nature Chemistry·Tracy L Lohr, Tobin J Marks
Oct 20, 2015·Chemical Reviews·Changzhi LiTao Zhang
Jun 9, 2018·Chemistry : a European Journal·Pierre-Adrien PayardMarc Pera-Titus
Jan 23, 2019·Organic & Biomolecular Chemistry·Joseph Becica, Graham E Dobereiner
Mar 3, 2015·Scientific Reports·Saikat KhamaruiDilip K Maiti
Jul 25, 2019·ChemSusChem·Bernhard M StadlerJohannes G de Vries
Jul 26, 2014·Angewandte Chemie·Michael C HaibachAlan S Goldman
Oct 2, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Zhijin LinMatthew J Allen
Apr 23, 2019·European Journal of Organic Chemistry·Wuyuan ZhangSandy Schmidt
Sep 23, 2020·Chembiochem : a European Journal of Chemical Biology·Fatma Feyza ÖzgenSandy Schmidt
Sep 30, 2018·Bioresource Technology·Hongliang WangBin Yang
Feb 23, 2020·Journal of the American Chemical Society·Yang SongWenbin Lin

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