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

Hu Li, Wenfeng Zhao, Wenshuai Dai, Jingxuan Long, Masaru Watanabe, Sebastian Meier*, Shunmugavel Saravanamurugan, Song Yang, Anders Riisager

*Corresponding author for this work

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Biomass deriatives are a class of oxygen-rich organic compounds, which can be selectively upgraded to various value-added molecules by partial or complete hydrogeneration over metal catalysts. Here, we show that Cs2CO2, a low-cost commercial chemical, enables the selective reduction of dicarbonyl compounds including bio-derived carboxides to monohydric esteres/amides, hydroxylamines or diols with high yields (82-99%) at room temperature using eco-friendly and equivalent hydrosilane as 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 selectives. Spectroscopic and computational studies eludicate reaction pathways with an emphasis on the role of endogenous siloxane. 
Original languageEnglish
JournalGreen Chemistry
Issue number23
Pages (from-to)5327-5335
Number of pages8
Publication statusPublished - 2018

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