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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
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TitleHighly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex
 
AuthorsLo, VKY1
Guo, Z1
Choi, MKW1
Yu, WY1 2
Huang, JS1
Che, CM1
 
Issue Date2012
 
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
 
CitationJournal Of The American Chemical Society, 2012, v. 134 n. 18, p. 7588-7591 [How to Cite?]
DOI: http://dx.doi.org/10.1021/ja3006989
 
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.
 
ISSN0002-7863
2012 Impact Factor: 10.677
2012 SCImago Journal Rankings: 5.182
 
DOIhttp://dx.doi.org/10.1021/ja3006989
 
ReferencesReferences in Scopus
 
DC FieldValue
dc.contributor.authorLo, VKY
 
dc.contributor.authorGuo, Z
 
dc.contributor.authorChoi, MKW
 
dc.contributor.authorYu, WY
 
dc.contributor.authorHuang, JS
 
dc.contributor.authorChe, CM
 
dc.date.accessioned2012-10-08T03:21:46Z
 
dc.date.available2012-10-08T03:21:46Z
 
dc.date.issued2012
 
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.
 
dc.description.natureLink_to_subscribed_fulltext
 
dc.identifier.citationJournal Of The American Chemical Society, 2012, v. 134 n. 18, p. 7588-7591 [How to Cite?]
DOI: http://dx.doi.org/10.1021/ja3006989
 
dc.identifier.citeulike10762465
 
dc.identifier.doihttp://dx.doi.org/10.1021/ja3006989
 
dc.identifier.epage7591
 
dc.identifier.hkuros204145
 
dc.identifier.issn0002-7863
2012 Impact Factor: 10.677
2012 SCImago Journal Rankings: 5.182
 
dc.identifier.issue18
 
dc.identifier.pmid22530941
 
dc.identifier.scopuseid_2-s2.0-84860864333
 
dc.identifier.spage7588
 
dc.identifier.urihttp://hdl.handle.net/10722/168627
 
dc.identifier.volume134
 
dc.languageeng
 
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
 
dc.publisher.placeUnited States
 
dc.relation.ispartofJournal of the American Chemical Society
 
dc.relation.referencesReferences in Scopus
 
dc.titleHighly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex
 
dc.typeArticle
 
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Author Affiliations
  1. Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong
  2. Hong Kong Polytechnic University