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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.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Björn Åkermark)
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, 16947-16954 p.Article 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, 16947-16954 p.
Keyword [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: diva2:587176
Funder
Knut and Alice Wallenberg Foundation
Available from: 2013-01-14 Created: 2013-01-14 Last updated: 2017-12-06Bibliographically 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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