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Article: Catalytic enantioselective oxidation of aromatic hydrocarbons with D 4-symmetric chiral ruthenium porphyrin catalysts

TitleCatalytic enantioselective oxidation of aromatic hydrocarbons with D 4-symmetric chiral ruthenium porphyrin catalysts
Authors
Issue Date2005
PublisherPergamon. 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?
AbstractThe [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 Identifierhttp://hdl.handle.net/10722/167971
ISSN
2015 Impact Factor: 2.108
2015 SCImago Journal Rankings: 0.806
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorZhang, Ren_US
dc.contributor.authorYu, WYen_US
dc.contributor.authorChe, CMen_US
dc.date.accessioned2012-10-08T03:13:35Z-
dc.date.available2012-10-08T03:13:35Z-
dc.date.issued2005en_US
dc.identifier.citationTetrahedron Asymmetry, 2005, v. 16 n. 21, p. 3520-3526en_US
dc.identifier.issn0957-4166en_US
dc.identifier.urihttp://hdl.handle.net/10722/167971-
dc.description.abstractThe [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.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetasyen_US
dc.relation.ispartofTetrahedron Asymmetryen_US
dc.titleCatalytic enantioselective oxidation of aromatic hydrocarbons with D 4-symmetric chiral ruthenium porphyrin catalystsen_US
dc.typeArticleen_US
dc.identifier.emailChe, CM:cmche@hku.hken_US
dc.identifier.authorityChe, CM=rp00670en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1016/j.tetasy.2005.08.059en_US
dc.identifier.scopuseid_2-s2.0-27944451047en_US
dc.identifier.hkuros117765-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-27944451047&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume16en_US
dc.identifier.issue21en_US
dc.identifier.spage3520en_US
dc.identifier.epage3526en_US
dc.identifier.isiWOS:000233784100013-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridZhang, R=7404865969en_US
dc.identifier.scopusauthoridYu, WY=7403913673en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US

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