Abstract: Deoxygenative upgrading of 5-hydromethylfurfural (HMF) into valuable chemicals has attracted intensive research interest in recent years, with product selectivity control remaining an important topic. Herein, TiO2 supported gold catalysts coated with a thin N-doped porous carbon (NPC) layer were developed via a polydopamine-coating-carbonization strategy and utilized for pathway-specific conversion of HMF into 5-methylfurfural (5-MF) with the use of renewable formic acid (FA) as the deoxygenation reagent. The as-fabricated Au/TiO2@NPC exhibited excellent catalytic performance with a high yield of 5-MF (>95%). The catalytic behavior of Au@NPC-based catalysts was shown to be correlated with the suitable combination of highly dispersed Au nanoparticles and favorable interfacial interactions in the Au@NPC core-shell hetero-nanoarchitectures, thereby facilitating the preferential esterification of HMF with FA and suppressing unproductive FA dehydrogenation, which promoted the selective formylation/decarboxylation of hydroxy-methyl group in HMF in a pathway-specific manner. The present NPC/metal interfacial engineering strategy may provide a potential guide for the rational design of advanced catalysts for a wide variety of heterogeneous catalysis processes in terms of the conversion of biomass source.
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With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;
General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.
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