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Application and mechanistic studies of a water-oxidation catalyst in alcohol oxidation by employing oxygen-transfer reagents
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-3153-748X
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Björn Åkermark)ORCID iD: 0000-0002-6089-5454
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Jan-Erling Bäckvall)
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2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 52, p. 16947-16954Article in journal (Refereed) Published
Abstract [en]

By using a dimeric ruthenium complex in combination with tert-butyl hydrogen peroxide (TBHP) as stoichiometric oxidant, a mild and efficient protocol for the oxidation of secondary benzylic alcohols was obtained, thereby giving the corresponding ketones in high yields within 4 h. However, in the oxidation of aliphatic alcohols, the TBHP protocol suffered from low conversions owing to a competing Ru-catalyzed disproportionation of the oxidant. Gratifyingly, by switching to Oxone (2 KHSO5KHSO4K2SO4 triple salt) as stoichiometric oxidant, a more efficient and robust system was obtained that allowed for the oxidation of a wide range of aliphatic and benzylic secondary alcohols, giving the corresponding ketones in excellent yields. The mechanism for these reactions is believed to involve a high-valent RuV–oxo species. We provide support for such an intermediate by means of mechanistic studies.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2012. Vol. 18, no 52, p. 16947-16954
Keywords [en]
alcohols, biphasic catalysis, oxidation, Oxone, ruthenium
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-86521DOI: 10.1002/chem.201202266OAI: oai:DiVA.org:su-86521DiVA, id: diva2:587176
Funder
Knut and Alice Wallenberg FoundationAvailable from: 2013-01-14 Created: 2013-01-14 Last updated: 2019-12-16Bibliographically approved

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Verho, OscarKärkäs, MarkusJohnston, EricÅkermark, TorbjörnBäckvall, Jan-E.Åkermark, Björn
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Department of Organic ChemistryDepartment of Materials and Environmental Chemistry (MMK)
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