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Application and mechanistic studies of a water-oxidation catalyst in alcohol oxidation by employing oxygen-transfer reagents
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-3153-748X
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-6089-5454
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
2012 (engelsk)Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, nr 52, s. 16947-16954Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2012. Vol. 18, nr 52, s. 16947-16954
Emneord [en]
alcohols, biphasic catalysis, oxidation, Oxone, ruthenium
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-86521DOI: 10.1002/chem.201202266ISI: 000312552300037OAI: oai:DiVA.org:su-86521DiVA, id: diva2:587176
Forskningsfinansiär
Knut and Alice Wallenberg FoundationTilgjengelig fra: 2013-01-14 Laget: 2013-01-14 Sist oppdatert: 2022-02-24bibliografisk kontrollert

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Verho, OscarDilenstam, Marléne D. V.Kärkäs, Markus D.Johnston, Eric V.Åkermark, TorbjörnBäckvall, Jan-E.Åkermark, Björn

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Verho, OscarDilenstam, Marléne D. V.Kärkäs, Markus D.Johnston, Eric V.Åkermark, TorbjörnBäckvall, Jan-E.Åkermark, Björn
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