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Article: Dichlororuthenium(IV) complex of meso-Tetrakis(2,6-dichlorophenyl) porphyrin: Active and robust catalyst for highly selective oxidation of arenes, Unsaturated steroids, and electron-deficient alkenes by using 2,6-dichloropyridine N-oxide

TitleDichlororuthenium(IV) complex of meso-Tetrakis(2,6-dichlorophenyl) porphyrin: Active and robust catalyst for highly selective oxidation of arenes, Unsaturated steroids, and electron-deficient alkenes by using 2,6-dichloropyridine N-oxide
Authors
KeywordsHomogeneous catalysis
Oxidation
Porphyrinoids
Ruthenium
Structure elucidation
Issue Date2005
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2005, v. 11 n. 13, p. 3899-3914 How to Cite?
Abstract[RuIV(2,6-Cl2tpp)Cl2], prepared in 90% yield from the reaction of [RuVI(2,6-Cl2tpp)O2] with Me3SiCl and structurally characterized by X-ray crystallography, is markedly superior to [RuIv(tmp)Cl2], [RuIV(ttp)Cl2], and [RuII(por)(CO)] (por = 2,6-Cl2tpp, F20-tpp, F28-tpp) as a catalyst for alkene epoxidation with 2,6-Cl2pyNO (2,6Cl2tpp = meso-tetrakis(2,6-dichlorophenyl)porphyrinato dianion; tmp = meso-tetramesitylporphyrinato dianion; ttp = meso-tetrakis(p-tolyl)porphyrinato dianion; F20-tpp = meso-tetrakis(pentafluorophenyl)porphyrinato dianion; F28-tpp = 2,3,7,8,12,13,17,18-octafluoro-5,10,15,20- tetrakis(pentafluorophenyl)-porphyrinato dianion). The "[Ru IV(2,6-Cl2tpp)Cl2] + 2,6-Cl 2pyNO" protocol oxidized, under acid-free conditions, a wide variety of hydrocarbons including 1) cycloalkenes, conjugated enynes, electron-deficient alkenes (to afford epoxides), 2) arenes (to afford quinones), and 3) Δ5-unsaturated steroids, Δ4-3- ketosteroids, and estratetraene derivatives (to afford epoxide/ketone derivatives of steroids) in up to 99% product yield within several hours with up to 100% substrate conversion and excellent regio- or diastereoselectivity. Catalyst [RuIv(2,6-Cl2tpp)Cl2] is remarkably active and robust toward the above oxidation reactions, and turnover numbers of up to 6.4 × 103, 2.0 × 104, and 1.6 × 104 were obtained for the oxidation of α,β-unsaturated ketones, arenes, and Δ5-unsaturated steroids, respectively. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/70092
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorZhang, JLen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:19:38Z-
dc.date.available2010-09-06T06:19:38Z-
dc.date.issued2005en_HK
dc.identifier.citationChemistry - A European Journal, 2005, v. 11 n. 13, p. 3899-3914en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70092-
dc.description.abstract[RuIV(2,6-Cl2tpp)Cl2], prepared in 90% yield from the reaction of [RuVI(2,6-Cl2tpp)O2] with Me3SiCl and structurally characterized by X-ray crystallography, is markedly superior to [RuIv(tmp)Cl2], [RuIV(ttp)Cl2], and [RuII(por)(CO)] (por = 2,6-Cl2tpp, F20-tpp, F28-tpp) as a catalyst for alkene epoxidation with 2,6-Cl2pyNO (2,6Cl2tpp = meso-tetrakis(2,6-dichlorophenyl)porphyrinato dianion; tmp = meso-tetramesitylporphyrinato dianion; ttp = meso-tetrakis(p-tolyl)porphyrinato dianion; F20-tpp = meso-tetrakis(pentafluorophenyl)porphyrinato dianion; F28-tpp = 2,3,7,8,12,13,17,18-octafluoro-5,10,15,20- tetrakis(pentafluorophenyl)-porphyrinato dianion). The "[Ru IV(2,6-Cl2tpp)Cl2] + 2,6-Cl 2pyNO" protocol oxidized, under acid-free conditions, a wide variety of hydrocarbons including 1) cycloalkenes, conjugated enynes, electron-deficient alkenes (to afford epoxides), 2) arenes (to afford quinones), and 3) Δ5-unsaturated steroids, Δ4-3- ketosteroids, and estratetraene derivatives (to afford epoxide/ketone derivatives of steroids) in up to 99% product yield within several hours with up to 100% substrate conversion and excellent regio- or diastereoselectivity. Catalyst [RuIv(2,6-Cl2tpp)Cl2] is remarkably active and robust toward the above oxidation reactions, and turnover numbers of up to 6.4 × 103, 2.0 × 104, and 1.6 × 104 were obtained for the oxidation of α,β-unsaturated ketones, arenes, and Δ5-unsaturated steroids, respectively. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.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/home/chemistryen_HK
dc.relation.ispartofChemistry - A European Journalen_HK
dc.subjectHomogeneous catalysisen_HK
dc.subjectOxidationen_HK
dc.subjectPorphyrinoidsen_HK
dc.subjectRutheniumen_HK
dc.subjectStructure elucidationen_HK
dc.titleDichlororuthenium(IV) complex of meso-Tetrakis(2,6-dichlorophenyl) porphyrin: Active and robust catalyst for highly selective oxidation of arenes, Unsaturated steroids, and electron-deficient alkenes by using 2,6-dichloropyridine N-oxideen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0947-6539&volume=11&spage=3899&epage=3914&date=2005&atitle=Dichlororuthenium(IV)+complex+of+meso-tetrakis(2,6-dichlorophenyl)+porphyrin:+Active+and+robust+catalyst+for+highly+selective+oxidation+of+arenes,+unsaturated+steroids,+and+electron-deficient+alkenes+by+using+2,6-dichloropyridine+N-oxideen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.200401008en_HK
dc.identifier.pmid15812875-
dc.identifier.scopuseid_2-s2.0-21244435594en_HK
dc.identifier.hkuros106838en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-21244435594&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume11en_HK
dc.identifier.issue13en_HK
dc.identifier.spage3899en_HK
dc.identifier.epage3914en_HK
dc.identifier.isiWOS:000230071100013-
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridZhang, JL=7601343511en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.citeulike7915415-

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