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Article: Ruthenium(II) porphyrin catalyzed imine aziridination and crystal structures of (meso-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II) complexes containing PhN=CH(p-ClPh), CPh2, and pyridine ligands

TitleRuthenium(II) porphyrin catalyzed imine aziridination and crystal structures of (meso-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II) complexes containing PhN=CH(p-ClPh), CPh2, and pyridine ligands
Authors
Issue Date2004
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/organometallics
Citation
Organometallics, 2004, v. 23 n. 1, p. 54-66 How to Cite?
AbstractA (meso-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II) complex of PhN=CH(p-ClPh) is prepared by reacting [Ru(F20-TPP)(CO)] (1) with a benzene solution of N-(p-chlorobenzylene)aniline. The crystal structure of {Ru(F20-TPP)(CO)[PhN=CH(p-ClPh)]} (10) shows the coordinated imine ligand in a cis configuration. Comparison with X-ray crystallographic data for [Ru(F20-TPP)(py)2] (11) revealed the axial Ru-N bond length of the imine complex (2.203 Å) to be slightly longer than that of the bis(pyridine) complex (2.108 Å). Spectral and structural data revealed the Ru-N(imine) bond to have single-bond character, and the Ru=C bond in [Ru(F20-TPP)(CPh2)] (7) has a bond distance of 1.842 Å, indicative of multiple-bond character. In the presence of diazo compounds, {Ru(F20-TPP)(CO)[PhN=CH-(p-ClPh)]} (10) and other related complexes mediated diastereoselective imine aziridination with product yields up to 86%. The mechanism is suggested to involve activation of the imine and diazo compounds by the ruthenium(II) porphyrin catalyst followed by nucleophilic addition of the imine to the diazo ester and subsequent cyclization to give the aziridine.
Persistent Identifierhttp://hdl.handle.net/10722/70329
ISSN
2015 Impact Factor: 4.186
2015 SCImago Journal Rankings: 2.043
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLi, Yen_HK
dc.contributor.authorChan, PWHen_HK
dc.contributor.authorZhu, NYen_HK
dc.contributor.authorChe, CMen_HK
dc.contributor.authorKwong, HLen_HK
dc.date.accessioned2010-09-06T06:21:51Z-
dc.date.available2010-09-06T06:21:51Z-
dc.date.issued2004en_HK
dc.identifier.citationOrganometallics, 2004, v. 23 n. 1, p. 54-66en_HK
dc.identifier.issn0276-7333en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70329-
dc.description.abstractA (meso-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II) complex of PhN=CH(p-ClPh) is prepared by reacting [Ru(F20-TPP)(CO)] (1) with a benzene solution of N-(p-chlorobenzylene)aniline. The crystal structure of {Ru(F20-TPP)(CO)[PhN=CH(p-ClPh)]} (10) shows the coordinated imine ligand in a cis configuration. Comparison with X-ray crystallographic data for [Ru(F20-TPP)(py)2] (11) revealed the axial Ru-N bond length of the imine complex (2.203 Å) to be slightly longer than that of the bis(pyridine) complex (2.108 Å). Spectral and structural data revealed the Ru-N(imine) bond to have single-bond character, and the Ru=C bond in [Ru(F20-TPP)(CPh2)] (7) has a bond distance of 1.842 Å, indicative of multiple-bond character. In the presence of diazo compounds, {Ru(F20-TPP)(CO)[PhN=CH-(p-ClPh)]} (10) and other related complexes mediated diastereoselective imine aziridination with product yields up to 86%. The mechanism is suggested to involve activation of the imine and diazo compounds by the ruthenium(II) porphyrin catalyst followed by nucleophilic addition of the imine to the diazo ester and subsequent cyclization to give the aziridine.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/organometallicsen_HK
dc.relation.ispartofOrganometallicsen_HK
dc.titleRuthenium(II) porphyrin catalyzed imine aziridination and crystal structures of (meso-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II) complexes containing PhN=CH(p-ClPh), CPh2, and pyridine ligandsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0276-7333&volume=23&spage=54&epage=66&date=2004&atitle=Ruthenium(II)+porphyrin+catalyzed+imine+aziridination+and+crystal+structures+of+(meso-Tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II)+complexes+containing+PhN=CH(p-ClPh),+CPH2,+and+pyridine+ligandsen_HK
dc.identifier.emailZhu, NY: nzhu@hkucc.hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hken_HK
dc.identifier.authorityZhu, NY=rp00845en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/om034128ben_HK
dc.identifier.scopuseid_2-s2.0-1642537532en_HK
dc.identifier.hkuros91659en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-1642537532&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume23en_HK
dc.identifier.issue1en_HK
dc.identifier.spage54en_HK
dc.identifier.epage66en_HK
dc.identifier.isiWOS:000187727600011-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridLi, Y=35187394200en_HK
dc.identifier.scopusauthoridChan, PWH=13607033800en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridKwong, HL=35569416300en_HK

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