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Article: Catalytic enantioselective oxidation of aromatic hydrocarbons with D 4-symmetric chiral ruthenium porphyrin catalysts
Title | Catalytic enantioselective oxidation of aromatic hydrocarbons with D 4-symmetric chiral ruthenium porphyrin catalysts |
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Authors | |
Issue Date | 2005 |
Publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasy |
Citation | Tetrahedron Asymmetry, 2005, v. 16 n. 21, p. 3520-3526 How to Cite? |
Abstract | The [RuII(D4-Por*)(CO)(MeOH)] (D 4-H2Por* = tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8- octahydro-1,4:5,8-dimethanoanthracen-9-yl]porphyrin) complex 1 is an effective catalyst for asymmetric hydroxylation of aromatic hydrocarbons with 2,6-dichloropyridine N-oxide (Cl2pyNO) as terminal oxidant. Up to 76% ee was achieved for the catalytic hydroxylation of 4-ethyltoluene, 1,1-diethylindan and benzylcyclopropane. Both electron-donating and -withdrawing substituents were found to accelerate the catalytic oxidation reaction, and a large primary H/D kinetic isotope effect (kH/kD = 11 at 298 K) was observed for the catalytic ethylbenzene-d10 oxidation. A mechanism involving rate-limiting hydrogen atom abstraction by reactive oxoruthenium species is postulated. © 2005 Elsevier Ltd. All rights reserved. |
Persistent Identifier | http://hdl.handle.net/10722/167971 |
ISSN | 2016 Impact Factor: 2.126 2020 SCImago Journal Rankings: 0.396 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Zhang, R | en_US |
dc.contributor.author | Yu, WY | en_US |
dc.contributor.author | Che, CM | en_US |
dc.date.accessioned | 2012-10-08T03:13:35Z | - |
dc.date.available | 2012-10-08T03:13:35Z | - |
dc.date.issued | 2005 | en_US |
dc.identifier.citation | Tetrahedron Asymmetry, 2005, v. 16 n. 21, p. 3520-3526 | en_US |
dc.identifier.issn | 0957-4166 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/167971 | - |
dc.description.abstract | The [RuII(D4-Por*)(CO)(MeOH)] (D 4-H2Por* = tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8- octahydro-1,4:5,8-dimethanoanthracen-9-yl]porphyrin) complex 1 is an effective catalyst for asymmetric hydroxylation of aromatic hydrocarbons with 2,6-dichloropyridine N-oxide (Cl2pyNO) as terminal oxidant. Up to 76% ee was achieved for the catalytic hydroxylation of 4-ethyltoluene, 1,1-diethylindan and benzylcyclopropane. Both electron-donating and -withdrawing substituents were found to accelerate the catalytic oxidation reaction, and a large primary H/D kinetic isotope effect (kH/kD = 11 at 298 K) was observed for the catalytic ethylbenzene-d10 oxidation. A mechanism involving rate-limiting hydrogen atom abstraction by reactive oxoruthenium species is postulated. © 2005 Elsevier Ltd. All rights reserved. | en_US |
dc.language | eng | en_US |
dc.publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasy | en_US |
dc.relation.ispartof | Tetrahedron Asymmetry | en_US |
dc.title | Catalytic enantioselective oxidation of aromatic hydrocarbons with D 4-symmetric chiral ruthenium porphyrin catalysts | en_US |
dc.type | Article | en_US |
dc.identifier.email | Che, CM:cmche@hku.hk | en_US |
dc.identifier.authority | Che, CM=rp00670 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1016/j.tetasy.2005.08.059 | en_US |
dc.identifier.scopus | eid_2-s2.0-27944451047 | en_US |
dc.identifier.hkuros | 117765 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-27944451047&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 16 | en_US |
dc.identifier.issue | 21 | en_US |
dc.identifier.spage | 3520 | en_US |
dc.identifier.epage | 3526 | en_US |
dc.identifier.isi | WOS:000233784100013 | - |
dc.publisher.place | United Kingdom | en_US |
dc.identifier.scopusauthorid | Zhang, R=7404865969 | en_US |
dc.identifier.scopusauthorid | Yu, WY=7403913673 | en_US |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_US |
dc.identifier.issnl | 0957-4166 | - |