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Article: Homogeneous [RuIII(Me3tacn)Cl3]-catalyzed alkene cis-dihydroxylation with aqueous hydrogen peroxide

TitleHomogeneous [RuIII(Me3tacn)Cl3]-catalyzed alkene cis-dihydroxylation with aqueous hydrogen peroxide
Authors
KeywordsAlkenes
Catalysis
Dihydroxylation
Oxidation
Ruthenium
Issue Date2008
PublisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/publish/en/journals/alphabeticIndex/2451
Citation
Chemistry - An Asian Journal, 2008, v. 3 n. 1, p. 70-77 How to Cite?
AbstractA simple and green method that uses [Ru(Me3tacn)Cl3] (1; Me3tacn=N,N′,N″-trimethyl-1,4,7-triazacyclononane) as catalyst,aqueous H2O2 as the terminal oxidant, and Al2O3 and NaCl as additives is effective in the cis-dihydroxylation of alkenes in aqueous tert-butanol. Unfunctionalized alkenes,including cycloalkenes, aliphat ic alkenes, and styrenes (14 examples) were selectively oxidized to their corresponding cis-diols in good to excellent yield (70-96%) based on substrate conversions of up to 100%. The preparation of cis-1,2-cycloheptanediol (119 g,91 % yield) and cis-1,2-cyclooctanediol (128 g,92 % yield) from cycloheptene and cyclooctene,respectively, on the 1-mol scale can be achieved by scaling up the reaction without modification. Results from Hammett correlation studies on the competitive oxidation of para-substituted styrenes (ρ=-0.97, R=0.988) and the detection of the cycloadduct [(Me 3tacn)ClRuHO2(C8H14)]+ by ESI-MS for the 1-catalyzed oxidation of cyclooctene to cis-1,2-cyclooctanediol are similar to those of the stoichiometric oxidation of alkenes by cis-[(Me 3tacn)-(CF3CO2)RuVIO2]+ through [3+2] cycloaddition (W.-P. Yip, W .-Y. Yu, N. Zhu, C.-M. Che, J. Am. Chem. Soc. 2005, 127,14239). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
Persistent Identifierhttp://hdl.handle.net/10722/70371
ISSN
2015 Impact Factor: 4.592
2015 SCImago Journal Rankings: 1.833
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYip, WPen_HK
dc.contributor.authorHo, CMen_HK
dc.contributor.authorZhu, Nen_HK
dc.contributor.authorLau, TCen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:22:14Z-
dc.date.available2010-09-06T06:22:14Z-
dc.date.issued2008en_HK
dc.identifier.citationChemistry - An Asian Journal, 2008, v. 3 n. 1, p. 70-77en_HK
dc.identifier.issn1861-4728en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70371-
dc.description.abstractA simple and green method that uses [Ru(Me3tacn)Cl3] (1; Me3tacn=N,N′,N″-trimethyl-1,4,7-triazacyclononane) as catalyst,aqueous H2O2 as the terminal oxidant, and Al2O3 and NaCl as additives is effective in the cis-dihydroxylation of alkenes in aqueous tert-butanol. Unfunctionalized alkenes,including cycloalkenes, aliphat ic alkenes, and styrenes (14 examples) were selectively oxidized to their corresponding cis-diols in good to excellent yield (70-96%) based on substrate conversions of up to 100%. The preparation of cis-1,2-cycloheptanediol (119 g,91 % yield) and cis-1,2-cyclooctanediol (128 g,92 % yield) from cycloheptene and cyclooctene,respectively, on the 1-mol scale can be achieved by scaling up the reaction without modification. Results from Hammett correlation studies on the competitive oxidation of para-substituted styrenes (ρ=-0.97, R=0.988) and the detection of the cycloadduct [(Me 3tacn)ClRuHO2(C8H14)]+ by ESI-MS for the 1-catalyzed oxidation of cyclooctene to cis-1,2-cyclooctanediol are similar to those of the stoichiometric oxidation of alkenes by cis-[(Me 3tacn)-(CF3CO2)RuVIO2]+ through [3+2] cycloaddition (W.-P. Yip, W .-Y. Yu, N. Zhu, C.-M. Che, J. Am. Chem. Soc. 2005, 127,14239). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.en_HK
dc.languageengen_HK
dc.publisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/publish/en/journals/alphabeticIndex/2451en_HK
dc.relation.ispartofChemistry - An Asian Journalen_HK
dc.subjectAlkenesen_HK
dc.subjectCatalysisen_HK
dc.subjectDihydroxylationen_HK
dc.subjectOxidationen_HK
dc.subjectRutheniumen_HK
dc.titleHomogeneous [RuIII(Me3tacn)Cl3]-catalyzed alkene cis-dihydroxylation with aqueous hydrogen peroxideen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1861-4728&volume=3&issue=1&spage=70&epage=77&date=2008&atitle=Homogeneous+[RuIII(Me3tacn)Cl3]-Catalyzed+Alkene+cis-Dihydroxylation+with+Aqueous+Hydrogen+Peroxideen_HK
dc.identifier.emailHo, CM: rickyho@hkucc.hku.hken_HK
dc.identifier.emailZhu, N: nzhu@hkucc.hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hken_HK
dc.identifier.authorityHo, CM=rp00705en_HK
dc.identifier.authorityZhu, N=rp00845en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/asia.200700237en_HK
dc.identifier.pmid17985328-
dc.identifier.scopuseid_2-s2.0-38449101996en_HK
dc.identifier.hkuros142363en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-38449101996&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume3en_HK
dc.identifier.issue1en_HK
dc.identifier.spage70en_HK
dc.identifier.epage77en_HK
dc.identifier.isiWOS:000252292100008-
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridYip, WP=8751048200en_HK
dc.identifier.scopusauthoridHo, CM=12807243800en_HK
dc.identifier.scopusauthoridZhu, N=7201449530en_HK
dc.identifier.scopusauthoridLau, TC=7102222310en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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