Reduction of Activated Alkenes by P III/P V Redox Cycling Catalysis

Abstract: 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.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Reduction of Activated Alkenes by P III/P V Redox Cycling Catalysis ; volume:59 ; number:7 ; year:2020 ; pages:2760-2763 ; extent:4 ; Angewandte Chemie / International edition. International edition ; 59, Heft 7 (2020), 2760-2763 (gesamt 4)

Contributors, Places and Time

• Creator: Longwitz, Lars ; Werner, Thomas

Further information

• DOI: 10.1002/anie.201912991
• URN: urn:nbn:de:101:1-2022061212503448164920
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:28 AM CEST