Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: silyl species enable reactivity
| Autor: | Song Yang, Wenfeng Zhao, Jingxuan Long, Anders Riisager, Sebastian Meier, Masaru Watanabe, Hu Li, Shunmugavel Saravanamurugan, Wenshuai Dai |
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| Rok vydání: | 2018 |
| Předmět: |
Silylation
010405 organic chemistry Hydride engineering.material 010402 general chemistry 01 natural sciences Pollution 0104 chemical sciences Silyl ether Catalysis chemistry.chemical_compound chemistry Siloxane engineering Environmental Chemistry Molecule Organic chemistry Reactivity (chemistry) Noble metal |
| Zdroj: | Li, H, Zhao, W, Dai, W, Long, J, Watanabe, M, Meier, S, Saravanamurugan, S, Yang, S & Riisager, A 2018, ' Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: Silyl species enable reactivity ', Green Chemistry, vol. 20, no. 23, pp. 5327-5335 . https://doi.org/10.1039/C8GC02934B |
| ISSN: | 1463-9270 1463-9262 |
| DOI: | 10.1039/c8gc02934b |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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