Reduction of Activated Alkenes by PIII/PV Redox Cycling Catalysis

dc.bibliographicCitation.firstPage2760eng
dc.bibliographicCitation.issue7eng
dc.bibliographicCitation.lastPage2763eng
dc.bibliographicCitation.volume59eng
dc.contributor.authorLongwitz, Lars
dc.contributor.authorWerner, Thomas
dc.date.accessioned2021-09-03T05:24:07Z
dc.date.available2021-09-03T05:24:07Z
dc.date.issued2019
dc.description.abstractThe 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. © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.eng
dc.description.versionpublishedVersioneng
dc.identifier.urihttps://oa.tib.eu/renate/handle/123456789/6682
dc.identifier.urihttps://doi.org/10.34657/5729
dc.language.isoengeng
dc.publisherWeinheim : Wiley-VCHeng
dc.relation.doihttps://doi.org/10.1002/anie.201912991
dc.relation.essn1521-3773
dc.relation.ispartofseriesAngewandte Chemie : a journal of the Gesellschaft Deutscher Chemiker : International edition 59 (2020), Nr. 7eng
dc.relation.issn0570-0833
dc.relation.issn1433-7851
dc.rights.licenseCC BY-NC-ND 4.0 Unportedeng
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/eng
dc.subjectalkeneseng
dc.subjectorganocatalysiseng
dc.subjectphosphoruseng
dc.subjectredox catalysiseng
dc.subjectreductioneng
dc.subject.ddc540eng
dc.titleReduction of Activated Alkenes by PIII/PV Redox Cycling Catalysiseng
dc.typearticleeng
dc.typeTexteng
dcterms.bibliographicCitation.journalTitleAngewandte Chemie : a journal of the Gesellschaft Deutscher Chemiker : International editioneng
tib.accessRightsopenAccesseng
wgl.contributorLIKATeng
wgl.subjectChemieeng
wgl.typeZeitschriftenartikeleng
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