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- Publisher Website: 10.1002/1521-3765(20020402)8:7<1554::AID-CHEM1554>3.0.CO;2-R
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Article: Dendritic ruthenium porphyrins: A new class of highly selective catalysts for alkene epoxidation and cyclopropanation
Title | Dendritic ruthenium porphyrins: A new class of highly selective catalysts for alkene epoxidation and cyclopropanation |
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Authors | |
Keywords | Cyclopropanation Dendrimers Epoxidation Homogenous catalysis Porphyrinoids Ruthenium |
Issue Date | 2002 |
Publisher | Wiley - 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? |
Abstract | Attachment 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 Identifier | http://hdl.handle.net/10722/69765 |
ISSN | 2023 Impact Factor: 3.9 2023 SCImago Journal Rankings: 1.058 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Zhang, JL | en_HK |
dc.contributor.author | Zhou, HB | en_HK |
dc.contributor.author | Huang, JS | en_HK |
dc.contributor.author | Che, CM | en_HK |
dc.date.accessioned | 2010-09-06T06:16:38Z | - |
dc.date.available | 2010-09-06T06:16:38Z | - |
dc.date.issued | 2002 | en_HK |
dc.identifier.citation | Chemistry - A European Journal, 2002, v. 8 n. 7, p. 1554-1562 | en_HK |
dc.identifier.issn | 0947-6539 | en_HK |
dc.identifier.uri | http://hdl.handle.net/10722/69765 | - |
dc.description.abstract | Attachment 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.language | eng | en_HK |
dc.publisher | Wiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry | en_HK |
dc.relation.ispartof | Chemistry - A European Journal | en_HK |
dc.subject | Cyclopropanation | en_HK |
dc.subject | Dendrimers | en_HK |
dc.subject | Epoxidation | en_HK |
dc.subject | Homogenous catalysis | en_HK |
dc.subject | Porphyrinoids | en_HK |
dc.subject | Ruthenium | en_HK |
dc.title | Dendritic ruthenium porphyrins: A new class of highly selective catalysts for alkene epoxidation and cyclopropanation | en_HK |
dc.type | Article | en_HK |
dc.identifier.openurl | http://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+cyclopropanation | en_HK |
dc.identifier.email | Huang, JS:jshuang@hkucc.hku.hk | en_HK |
dc.identifier.email | Che, CM:cmche@hku.hk | en_HK |
dc.identifier.authority | Huang, JS=rp00709 | en_HK |
dc.identifier.authority | Che, CM=rp00670 | en_HK |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/1521-3765(20020402)8:7<1554::AID-CHEM1554>3.0.CO;2-R | en_HK |
dc.identifier.scopus | eid_2-s2.0-0037006824 | en_HK |
dc.identifier.hkuros | 72422 | en_HK |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0037006824&selection=ref&src=s&origin=recordpage | en_HK |
dc.identifier.volume | 8 | en_HK |
dc.identifier.issue | 7 | en_HK |
dc.identifier.spage | 1554 | en_HK |
dc.identifier.epage | 1562 | en_HK |
dc.identifier.isi | WOS:000174843500008 | - |
dc.publisher.place | Germany | en_HK |
dc.identifier.scopusauthorid | Zhang, JL=7601343511 | en_HK |
dc.identifier.scopusauthorid | Zhou, HB=7404742589 | en_HK |
dc.identifier.scopusauthorid | Huang, JS=7407192639 | en_HK |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_HK |
dc.identifier.issnl | 0947-6539 | - |