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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Abstract

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
Volume20
Issue number23
Pages (from-to)5327-5335
Number of pages8
ISSN1463-9262
DOIs
Publication statusPublished - 2018

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