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Article: Stoichiornetric and catalytic oxidations of alkanes and alcohols mediated by highly oxidizing ruthenium-oxo complexes bearing 6,6'-dichloro-2,2'-bipyridine

TitleStoichiornetric and catalytic oxidations of alkanes and alcohols mediated by highly oxidizing ruthenium-oxo complexes bearing 6,6'-dichloro-2,2'-bipyridine
Authors
Issue Date2000
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2000, v. 65 n. 23, p. 7996-8000 How to Cite?
AbstractThe ruthenium(II) complex cis-[Ru(6,6'-Cl 2bpy) 2(OH 2) 2](CF 3SO 3) 2 (1) is a robust catalyst for C-H bond oxidations of hydrocarbons, including linear alkanes, using tert-butyl hydroperoxide (TBHP) as terminal oxidant. Alcohols can be oxidized by the '1 + TBHP' protocol to the corresponding aldehydes/ketones with high product yields at ambient temperature. Oxidation of 1 with Ce(IV) in aqueous solution affords cis-[Ru(VI)(6,6'-Cl 2bpy) 2O 2] 2+, which is isolated as a green/yellow perchlorate salt (2). Complex 2 is a powerful stoichiometric oxidant for cycloalkane oxidations under mild conditions. Oxidation of cis-decalin is highly stereoretentive; cis-decalinol is obtained in high yield, and formation of trans-decalinol is not observed. Mechanistic studies showing a large primary kinetic isotope effect suggest a hydrogen-atom abstraction pathway. The relative reactivities of cycloalkanes toward oxidation by 2 have been examined through competitive experiments, and comparisons with Gif-type processes are presented.
Persistent Identifierhttp://hdl.handle.net/10722/167661
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChe, CMen_US
dc.contributor.authorCheng, KWen_US
dc.contributor.authorChan, MCWen_US
dc.contributor.authorLau, TCen_US
dc.contributor.authorMak, CKen_US
dc.date.accessioned2012-10-08T03:09:34Z-
dc.date.available2012-10-08T03:09:34Z-
dc.date.issued2000en_US
dc.identifier.citationJournal Of Organic Chemistry, 2000, v. 65 n. 23, p. 7996-8000en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/167661-
dc.description.abstractThe ruthenium(II) complex cis-[Ru(6,6'-Cl 2bpy) 2(OH 2) 2](CF 3SO 3) 2 (1) is a robust catalyst for C-H bond oxidations of hydrocarbons, including linear alkanes, using tert-butyl hydroperoxide (TBHP) as terminal oxidant. Alcohols can be oxidized by the '1 + TBHP' protocol to the corresponding aldehydes/ketones with high product yields at ambient temperature. Oxidation of 1 with Ce(IV) in aqueous solution affords cis-[Ru(VI)(6,6'-Cl 2bpy) 2O 2] 2+, which is isolated as a green/yellow perchlorate salt (2). Complex 2 is a powerful stoichiometric oxidant for cycloalkane oxidations under mild conditions. Oxidation of cis-decalin is highly stereoretentive; cis-decalinol is obtained in high yield, and formation of trans-decalinol is not observed. Mechanistic studies showing a large primary kinetic isotope effect suggest a hydrogen-atom abstraction pathway. The relative reactivities of cycloalkanes toward oxidation by 2 have been examined through competitive experiments, and comparisons with Gif-type processes are presented.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.titleStoichiornetric and catalytic oxidations of alkanes and alcohols mediated by highly oxidizing ruthenium-oxo complexes bearing 6,6'-dichloro-2,2'-bipyridineen_US
dc.typeArticleen_US
dc.identifier.emailChe, CM:cmche@hku.hken_US
dc.identifier.authorityChe, CM=rp00670en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jo0010126en_US
dc.identifier.scopuseid_2-s2.0-0034680620en_US
dc.identifier.hkuros59513-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0034680620&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume65en_US
dc.identifier.issue23en_US
dc.identifier.spage7996en_US
dc.identifier.epage8000en_US
dc.identifier.isiWOS:000165491300040-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US
dc.identifier.scopusauthoridCheng, KW=36439221300en_US
dc.identifier.scopusauthoridChan, MCW=7402598116en_US
dc.identifier.scopusauthoridLau, TC=7102222310en_US
dc.identifier.scopusauthoridMak, CK=7102876260en_US

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