期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 7, 页码 2760-2763出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912991
关键词
alkenes; organocatalysis; phosphorus; redox catalysis; reduction
资金
- Leibniz ScienceCampus Phosphorus Research Rostock Funding Source: Medline
The carbon-carbon double bond of unsaturated carbonyl compounds was readily reduced by using a phosphetane oxide catalyst in the presence of a simple organosilane as the terminal reductant and water as the hydrogen source. Quantitative hydrogenation was observed when 1.0 mol % of a methyl-substituted phosphetane oxide was employed as the catalyst. The procedure is highly selective towards activated double bonds, tolerating a variety of functional groups that are usually prone to reduction. In total, 25 alkenes and two alkynes were hydrogenated to the corresponding alkanes in excellent yields of up to 99 %. Notably, less active poly(methylhydrosiloxane) could also be utilized as the terminal reductant. Mechanistic investigations revealed the phosphane as the catalyst resting state and a protonation/deprotonation sequence as the crucial step in the catalytic cycle.
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