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Article: Dendritic ruthenium porphyrins: A new class of highly selective catalysts for alkene epoxidation and cyclopropanation

TitleDendritic ruthenium porphyrins: A new class of highly selective catalysts for alkene epoxidation and cyclopropanation
Authors
KeywordsCyclopropanation
Dendrimers
Epoxidation
Homogenous catalysis
Porphyrinoids
Ruthenium
Issue Date2002
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, 2002, v. 8 n. 7, p. 1554-1562 How to Cite?
AbstractAttachment of Fréchet-type poly(benzyl ether) dendrons [G-n] to carbonylruthenium(II) meso-tetraphenylporphyrin (5) using covalent etheric bonds forms a series of dendritic ruthenium(II) porphyrins 5-[G-n]m (m=4, n=1, 2; m=8, n=0-2). The attachment was realized by treating the carbonylruthenium(II) complex of 5,10,15,20-tetrakis(4′-hydroxyphenyl)porphyrin or 5,10,15,20-tetrakis(3′,5′-dihydroxyphenyl)porphyrin with [G-n] OSO2Me in refluxing dry acetone in the presence of potassium carbonate and [18]crown-6. Complexes 5-[G-n]m were characterized by UV/Vis, IR, and NMR spectroscopy and mass spectrometry. All of the dendritic ruthenium porphyrins are highly selective catalysts for epoxidation of alkenes with 2,6-dichloropyridine N-oxide (Cl2pyNO). The chemo- or diastereoselectivity increases with the generation number of the dendron and the number of dendrons attached to 5, and complex 5-[G-2]8 exhibits remarkable selectivity or turnover number in catalyzing the Cl2pyNO epoxidation of a variety of alkene substrates including styrene, trans-/cis-stilbene, 2,2-dimethylchromene, cyclooctene, and unsaturated steroids such as cholesteryl esters and estratetraene derivative. The cyclopropanation of styrene and its para-substituted derivatives with ethyl diazoacetate catalyzed by 5-[G-2]8 is highly trans selective.
Persistent Identifierhttp://hdl.handle.net/10722/69765
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.authorZhou, HBen_HK
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:16:38Z-
dc.date.available2010-09-06T06:16:38Z-
dc.date.issued2002en_HK
dc.identifier.citationChemistry - A European Journal, 2002, v. 8 n. 7, p. 1554-1562en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69765-
dc.description.abstractAttachment of Fréchet-type poly(benzyl ether) dendrons [G-n] to carbonylruthenium(II) meso-tetraphenylporphyrin (5) using covalent etheric bonds forms a series of dendritic ruthenium(II) porphyrins 5-[G-n]m (m=4, n=1, 2; m=8, n=0-2). The attachment was realized by treating the carbonylruthenium(II) complex of 5,10,15,20-tetrakis(4′-hydroxyphenyl)porphyrin or 5,10,15,20-tetrakis(3′,5′-dihydroxyphenyl)porphyrin with [G-n] OSO2Me in refluxing dry acetone in the presence of potassium carbonate and [18]crown-6. Complexes 5-[G-n]m were characterized by UV/Vis, IR, and NMR spectroscopy and mass spectrometry. All of the dendritic ruthenium porphyrins are highly selective catalysts for epoxidation of alkenes with 2,6-dichloropyridine N-oxide (Cl2pyNO). The chemo- or diastereoselectivity increases with the generation number of the dendron and the number of dendrons attached to 5, and complex 5-[G-2]8 exhibits remarkable selectivity or turnover number in catalyzing the Cl2pyNO epoxidation of a variety of alkene substrates including styrene, trans-/cis-stilbene, 2,2-dimethylchromene, cyclooctene, and unsaturated steroids such as cholesteryl esters and estratetraene derivative. The cyclopropanation of styrene and its para-substituted derivatives with ethyl diazoacetate catalyzed by 5-[G-2]8 is highly trans selective.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.subjectCyclopropanationen_HK
dc.subjectDendrimersen_HK
dc.subjectEpoxidationen_HK
dc.subjectHomogenous catalysisen_HK
dc.subjectPorphyrinoidsen_HK
dc.subjectRutheniumen_HK
dc.titleDendritic ruthenium porphyrins: A new class of highly selective catalysts for alkene epoxidation and cyclopropanationen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0947-6539&volume=8&issue=7&spage=1554&epage=1562&date=2002&atitle=Dendritic+ruthenium+porphyrins:++a+new+class+of+highly+selective+catalysts+for+alkene+epoxidation+and+cyclopropanationen_HK
dc.identifier.emailHuang, JS:jshuang@hkucc.hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/1521-3765(20020402)8:7<1554::AID-CHEM1554>3.0.CO;2-Ren_HK
dc.identifier.scopuseid_2-s2.0-0037006824en_HK
dc.identifier.hkuros72422en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037006824&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume8en_HK
dc.identifier.issue7en_HK
dc.identifier.spage1554en_HK
dc.identifier.epage1562en_HK
dc.identifier.isiWOS:000174843500008-
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridZhang, JL=7601343511en_HK
dc.identifier.scopusauthoridZhou, HB=7404742589en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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