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Article: Elevated catalytic activity of ruthenium(II)–porphyrin-catalyzed carbene/nitrene transfer and insertion reactions with N-heterocyclic carbene ligands

TitleElevated catalytic activity of ruthenium(II)–porphyrin-catalyzed carbene/nitrene transfer and insertion reactions with N-heterocyclic carbene ligands
Authors
KeywordsCarbene transfer
Ligand effects
N-heterocyclic carbenes
Nitrene transfer
Ruthenium
Issue Date2014
PublisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www3.interscience.wiley.com/journal/26737/home
Citation
Angewandte Chemie (International Edition), 2014, v. 53 n. 11, p. 2982-2987 How to Cite?
AbstractBis(NHC)ruthenium(II)–porphyrin complexes were designed, synthesized, and characterized. Owing to the strong donor strength of axial NHC ligands in stabilizing the trans M[DOUBLE BOND]CRR′/M[DOUBLE BOND]NR moiety, these complexes showed unprecedently high catalytic activity towards alkene cyclopropanation, carbene C[BOND]H, N[BOND]H, S[BOND]H, and O[BOND]H insertion, alkene aziridination, and nitrene C[BOND]H insertion with turnover frequencies up to 1950 min−1. The use of chiral [Ru(D4-Por)(BIMe)2] (1 g) as a catalyst led to highly enantioselective carbene/nitrene transfer and insertion reactions with up to 98 % ee. Carbene modification of the N terminus of peptides at 37 °C was possible. DFT calculations revealed that the trans axial NHC ligand facilitates the decomposition of diazo compounds by stabilizing the metal–carbene reaction intermediate.
Persistent Identifierhttp://hdl.handle.net/10722/209522
ISSN
2015 Impact Factor: 11.709
2015 SCImago Journal Rankings: 6.229
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorChan, KH-
dc.contributor.authorGuan, X-
dc.contributor.authorLo, VKY-
dc.contributor.authorChe, CM-
dc.date.accessioned2015-04-24T08:18:02Z-
dc.date.available2015-04-24T08:18:02Z-
dc.date.issued2014-
dc.identifier.citationAngewandte Chemie (International Edition), 2014, v. 53 n. 11, p. 2982-2987-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/209522-
dc.description.abstractBis(NHC)ruthenium(II)–porphyrin complexes were designed, synthesized, and characterized. Owing to the strong donor strength of axial NHC ligands in stabilizing the trans M[DOUBLE BOND]CRR′/M[DOUBLE BOND]NR moiety, these complexes showed unprecedently high catalytic activity towards alkene cyclopropanation, carbene C[BOND]H, N[BOND]H, S[BOND]H, and O[BOND]H insertion, alkene aziridination, and nitrene C[BOND]H insertion with turnover frequencies up to 1950 min−1. The use of chiral [Ru(D4-Por)(BIMe)2] (1 g) as a catalyst led to highly enantioselective carbene/nitrene transfer and insertion reactions with up to 98 % ee. Carbene modification of the N terminus of peptides at 37 °C was possible. DFT calculations revealed that the trans axial NHC ligand facilitates the decomposition of diazo compounds by stabilizing the metal–carbene reaction intermediate.-
dc.languageeng-
dc.publisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www3.interscience.wiley.com/journal/26737/home-
dc.relation.ispartofAngewandte Chemie (International Edition)-
dc.subjectCarbene transfer-
dc.subjectLigand effects-
dc.subjectN-heterocyclic carbenes-
dc.subjectNitrene transfer-
dc.subjectRuthenium-
dc.titleElevated catalytic activity of ruthenium(II)–porphyrin-catalyzed carbene/nitrene transfer and insertion reactions with N-heterocyclic carbene ligands-
dc.typeArticle-
dc.identifier.emailGuan, X: xgguan@hku.hk-
dc.identifier.emailLo, VKY: vkylo@hku.hk-
dc.identifier.emailChe, CM: cmche@hku.hk-
dc.identifier.authorityChe, CM=rp00670-
dc.identifier.doi10.1002/anie.201309888-
dc.identifier.pmid24520042-
dc.identifier.hkuros232218-
dc.identifier.volume53-
dc.identifier.issue11-
dc.identifier.spage2982-
dc.identifier.epage2987-
dc.identifier.isiWOS:000332270000016-
dc.publisher.placeGermany-

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