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Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: silyl species enable reactivity

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Abstract

Biomass derivatives are a class of oxygen-rich organic compounds, which can be selectively upgraded to various value-added molecules by partial or complete hydrogenation over metal catalysts. Here, we show that Cs2CO3, a low-cost commercial chemical, enables the selective reduction of dicarbonyl compounds including bio-derived carboxides to monohydric esters/amides, hydroxylamines or diols with high yields (82–99%) at room temperature using eco-friendly and equivalent hydrosilane as a hydride donor. The in situ formation of silyl ether enables the developed catalytic system to tolerate other unsaturated groups and permits a wide substrate scope with high selectivities. Spectroscopic and computational studies elucidate reaction pathways with an emphasis on the role of endogenous siloxane.

Graphical abstract: Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: silyl species enable reactivity

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Publication details

The article was received on 16 Sep 2018, accepted on 26 Oct 2018 and first published on 26 Oct 2018


Article type: Paper
DOI: 10.1039/C8GC02934B
Citation: Green Chem., 2018, Advance Article
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    Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: silyl species enable reactivity

    H. Li, W. Zhao, W. Dai, J. Long, M. Watanabe, S. Meier, S. Saravanamurugan, S. Yang and A. Riisager, Green Chem., 2018, Advance Article , DOI: 10.1039/C8GC02934B

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