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Article: Syntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation

TitleSyntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation
Authors
KeywordsAllylic Substitution
Copper
Cyclopropanation
Palladium
Pyridyl
Issue Date2006
PublisherElsevier SA. The Journal's web site is located at http://www.elsevier.com/locate/jorganchem
Citation
Journal Of Organometallic Chemistry, 2006, v. 691 n. 26, p. 5676-5684 How to Cite?
AbstractNew chiral C1-symmetric bidentate ligands, which possess two different nitrogen heterocycles, 1,3-thiazolyl, 1-methylimidazolyl or pyrazinyl and one pyridyl group, were prepared by Kröhnke condensation in 36-59% overall yield. Stable Pd(II)-allyl and Cu(II) chloride complexes formed by some of the ligands were obtained in 60-65% yields. X-ray crystal structure analysis of a copper(II) complex having 1-methylimidazolyl group indicated that it is a μ-chloro bridge dimer. The Pd(II)-allyl complexes were found to be active catalysts in the asymmetric allylic substitution of 1,3-diphenylprop-2-enyl acetate. The best result observed was 85% e.e. and 99% isolated yield. In addition, the in situ generated Cu(OTf)2 complexes were found to be active catalysts in cyclopropanation of styrene with ethyl diazoacetate. © 2006 Elsevier B.V. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/69088
ISSN
2015 Impact Factor: 2.336
2015 SCImago Journal Rankings: 0.732
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorTeng, PFen_HK
dc.contributor.authorTsang, CSen_HK
dc.contributor.authorYeung, HLen_HK
dc.contributor.authorWong, WLen_HK
dc.contributor.authorWong, WTen_HK
dc.contributor.authorKwong, HLen_HK
dc.date.accessioned2010-09-06T06:10:27Z-
dc.date.available2010-09-06T06:10:27Z-
dc.date.issued2006en_HK
dc.identifier.citationJournal Of Organometallic Chemistry, 2006, v. 691 n. 26, p. 5676-5684en_HK
dc.identifier.issn0022-328Xen_HK
dc.identifier.urihttp://hdl.handle.net/10722/69088-
dc.description.abstractNew chiral C1-symmetric bidentate ligands, which possess two different nitrogen heterocycles, 1,3-thiazolyl, 1-methylimidazolyl or pyrazinyl and one pyridyl group, were prepared by Kröhnke condensation in 36-59% overall yield. Stable Pd(II)-allyl and Cu(II) chloride complexes formed by some of the ligands were obtained in 60-65% yields. X-ray crystal structure analysis of a copper(II) complex having 1-methylimidazolyl group indicated that it is a μ-chloro bridge dimer. The Pd(II)-allyl complexes were found to be active catalysts in the asymmetric allylic substitution of 1,3-diphenylprop-2-enyl acetate. The best result observed was 85% e.e. and 99% isolated yield. In addition, the in situ generated Cu(OTf)2 complexes were found to be active catalysts in cyclopropanation of styrene with ethyl diazoacetate. © 2006 Elsevier B.V. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherElsevier SA. The Journal's web site is located at http://www.elsevier.com/locate/jorganchemen_HK
dc.relation.ispartofJournal of Organometallic Chemistryen_HK
dc.subjectAllylic Substitutionen_HK
dc.subjectCopperen_HK
dc.subjectCyclopropanationen_HK
dc.subjectPalladiumen_HK
dc.subjectPyridylen_HK
dc.titleSyntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanationen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-328X&volume=691&spage=5664&epage=5672&date=2006&atitle=Syntheses+of+C1-+Symmetric+Bidentate+Ligands+having+Pyridyl+and+1,3-Thiazolyl,+1-Methylimidazolyl+or+Pyrazinyl+Donor+Groups+for+Enantioselective+Palladium-catalyzed+Allylic+Substitution+and+Copper-catalyzed+Cyclopropanationen_HK
dc.identifier.emailWong, WT: wtwong@hku.hken_HK
dc.identifier.authorityWong, WT=rp00811en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.jorganchem.2006.06.050en_HK
dc.identifier.scopuseid_2-s2.0-33751342266en_HK
dc.identifier.hkuros127615en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-33751342266&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume691en_HK
dc.identifier.issue26en_HK
dc.identifier.spage5676en_HK
dc.identifier.epage5684en_HK
dc.identifier.isiWOS:000243267300018-
dc.publisher.placeSwitzerlanden_HK
dc.identifier.scopusauthoridTeng, PF=7006192221en_HK
dc.identifier.scopusauthoridTsang, CS=13103217900en_HK
dc.identifier.scopusauthoridYeung, HL=13103321700en_HK
dc.identifier.scopusauthoridWong, WL=7403971961en_HK
dc.identifier.scopusauthoridWong, WT=7403973084en_HK
dc.identifier.scopusauthoridKwong, HL=35569416300en_HK

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