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Article: Palladium(II)-catalyzed oxidative cascade cyclization reactions of anilides and anilines: Scope and mechanistic investigations

TitlePalladium(II)-catalyzed oxidative cascade cyclization reactions of anilides and anilines: Scope and mechanistic investigations
Authors
Keywordscyclizations
domino reactions
homogeneous catalysis
palladium
reaction mechanism
Issue Date2011
PublisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/publish/en/journals/alphabeticIndex/2451
Citation
Chemistry - An Asian Journal, 2011, v. 6 n. 8, p. 2166-2175 How to Cite?
AbstractWith Pd(OAc) 2/pyridine as the catalyst system and molecular oxygen as a green oxidant, acrylanilides and N-allylanilines undergo oxidative cascade cyclization to form heterocyclic rings in high yields. This methodology is applicable to acrylanilides of different substitution patterns on olefinic units. Mechanistic studies revealed that cyclization of acrylanilides proceeded through an intramolecular syn-amidopalladation pathway. The reversible nature of amidopalladation serves as a "scavenging process" to prevent β-hydride elimination from occurring halfway through the catalytic cycle, thus favoring the formation of cascade cyclization products. In addition, internal coordination between an σ-alkylpalladium species and a tethered olefinic C=C double bond also appears to disfavor β-hydride elimination. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/139021
ISSN
2015 Impact Factor: 4.592
2015 SCImago Journal Rankings: 1.833
ISI Accession Number ID
Funding AgencyGrant Number
University of Hong Kong
Hong Kong Research Grants CouncilHKU 705807P
Funding Information:

This work was supported financially by the University of Hong Kong and the Hong Kong Research Grants Council (HKU 705807P).

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorYip, KTen_HK
dc.contributor.authorYang, Den_HK
dc.date.accessioned2011-09-23T05:44:10Z-
dc.date.available2011-09-23T05:44:10Z-
dc.date.issued2011en_HK
dc.identifier.citationChemistry - An Asian Journal, 2011, v. 6 n. 8, p. 2166-2175en_HK
dc.identifier.issn1861-4728en_HK
dc.identifier.urihttp://hdl.handle.net/10722/139021-
dc.description.abstractWith Pd(OAc) 2/pyridine as the catalyst system and molecular oxygen as a green oxidant, acrylanilides and N-allylanilines undergo oxidative cascade cyclization to form heterocyclic rings in high yields. This methodology is applicable to acrylanilides of different substitution patterns on olefinic units. Mechanistic studies revealed that cyclization of acrylanilides proceeded through an intramolecular syn-amidopalladation pathway. The reversible nature of amidopalladation serves as a "scavenging process" to prevent β-hydride elimination from occurring halfway through the catalytic cycle, thus favoring the formation of cascade cyclization products. In addition, internal coordination between an σ-alkylpalladium species and a tethered olefinic C=C double bond also appears to disfavor β-hydride elimination. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.en_HK
dc.languageengen_US
dc.publisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/publish/en/journals/alphabeticIndex/2451en_HK
dc.relation.ispartofChemistry - An Asian Journalen_HK
dc.subjectcyclizationsen_HK
dc.subjectdomino reactionsen_HK
dc.subjecthomogeneous catalysisen_HK
dc.subjectpalladiumen_HK
dc.subjectreaction mechanismen_HK
dc.titlePalladium(II)-catalyzed oxidative cascade cyclization reactions of anilides and anilines: Scope and mechanistic investigationsen_HK
dc.typeArticleen_HK
dc.identifier.emailYip, KT: billyyip@graduate.hku.hken_HK
dc.identifier.emailYang, D: yangdan@hku.hken_HK
dc.identifier.authorityYip, KT=rp00832en_HK
dc.identifier.authorityYang, D=rp00825en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/asia.201100242en_HK
dc.identifier.pmid21656692-
dc.identifier.scopuseid_2-s2.0-79961066633en_HK
dc.identifier.hkuros196044en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-79961066633&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume6en_HK
dc.identifier.issue8en_HK
dc.identifier.spage2166en_HK
dc.identifier.epage2175en_HK
dc.identifier.isiWOS:000294112200041-
dc.publisher.placeGermanyen_HK
dc.relation.projectDeveloping Palladium-Catalyzed Asymmetric Tandem Oxidative Cyclization Reactions for Organic Synthesis-
dc.identifier.scopusauthoridYip, KT=10440172200en_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK

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