期刊
JOURNAL OF CATALYSIS
卷 371, 期 -, 页码 153-160出版社
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2019.01.034
关键词
Pd/C catalysis; Reaction mechanism; alpha-Alkylation; Heterogeneous catalysis; In-situ IR; Kinetics; C-C bond formation
资金
- Independent Research Fund Denmark [6111-00237]
- Villum fonden [13158]
- Haldor Topsoe A/S
- Lund beck Foundation [R250-2017-1292]
The alpha-alkylation of ketones with alcohols represents a green strategy for the formation of crucial carbon-carbon bonds since it only produces water as byproduct. In terms of reaction mechanism, the evidence for homogeneous catalysis supports a catalytic hydrogen-borrowing pathway; however, the reaction mechanism has not been investigated for heterogeneous Pd/C catalysts. Here, we report an improved method for alpha-alkylation of ketones with alcohols using commercially available Pd/C, ubiquitous in organic synthesis labs, as catalyst. The reaction conditions are mild compared to state-of-the-art for both homoand heterogeneous catalysts, and the developed conditions produces quantitative yields for most ketones and alcohols. A hot filtration experiment and recycling of the catalyst supports the heterogeneous nature of catalysis. Importantly, the reaction mechanism is studied for the first time by a combination of stoichiometric experiments and kinetic analyses by in-situ IR (React-IR). (C) 2019 Elsevier Inc. All rights reserved.
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