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Article: Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex

TitleHighly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex
Authors
Issue Date2012
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 2012, v. 134 n. 18, p. 7588-7591 How to Cite?
Abstract
Complex [(p-cymene)Ru(η 1-O 2CCF 3) 2(OH 2)] mediated transformation of α-diazoacetamides ArCH 2N(C(CH 3) 3)C(O)CHN 2 to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity. © 2012 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168627
ISSN
2013 Impact Factor: 11.444
ISI Accession Number ID
References

 

Author Affiliations
  1. Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong
  2. Hong Kong Polytechnic University
DC FieldValueLanguage
dc.contributor.authorLo, VKYen_US
dc.contributor.authorGuo, Zen_US
dc.contributor.authorChoi, MKWen_US
dc.contributor.authorYu, WYen_US
dc.contributor.authorHuang, JSen_US
dc.contributor.authorChe, CMen_US
dc.date.accessioned2012-10-08T03:21:46Z-
dc.date.available2012-10-08T03:21:46Z-
dc.date.issued2012en_US
dc.identifier.citationJournal Of The American Chemical Society, 2012, v. 134 n. 18, p. 7588-7591en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/168627-
dc.description.abstractComplex [(p-cymene)Ru(η 1-O 2CCF 3) 2(OH 2)] mediated transformation of α-diazoacetamides ArCH 2N(C(CH 3) 3)C(O)CHN 2 to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity. © 2012 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_US
dc.relation.ispartofJournal of the American Chemical Societyen_US
dc.titleHighly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complexen_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.doi10.1021/ja3006989en_US
dc.identifier.pmid22530941-
dc.identifier.scopuseid_2-s2.0-84860864333en_US
dc.identifier.hkuros204145-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-84860864333&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume134en_US
dc.identifier.issue18en_US
dc.identifier.spage7588en_US
dc.identifier.epage7591en_US
dc.identifier.isiWOS:000303696200004-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridLo, VKY=13406071200en_US
dc.identifier.scopusauthoridGuo, Z=36554069300en_US
dc.identifier.scopusauthoridChoi, MKW=7402093591en_US
dc.identifier.scopusauthoridYu, WY=7403913673en_US
dc.identifier.scopusauthoridHuang, JS=54964622200en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US
dc.identifier.citeulike10762465-

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