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Article: Convenient entry to mono- and dinuclear palladium(II) benzothiazolin-2- ylidene complexes and their activities toward Heck Coupling

TitleConvenient entry to mono- and dinuclear palladium(II) benzothiazolin-2- ylidene complexes and their activities toward Heck Coupling
Authors
Issue Date2006
Citation
Organometallics, 2006, v. 25, n. 21, p. 5105-5112 How to Cite?
AbstractUnder solventless conditions, benzothiazole reacts with benzyl bromide to give near-quantitative yield of the salt W-benzylbenzothiazolium bromide (A), which is a convenient air-stable heterocyclic carbene precursor. Treatment of A with Pd(OAc)2 in CH3CN affords the bis(carbene) complex cis-[PdBr2(NHC)2] (1) (NHC = N-benzylbenzothiazolin-2- ylidene). In DMSO, this reaction yields an unprecedented dinuclear N,S-heterocyclic carbene complex, [PdBr2(NHC)]2 (2). Complex 2 undergoes bridge cleavage reactions with CH3CN and DMF to give the mononuclear and solvated monocarbene complexes trans-[PdBr 2(NHC)(Solv)] [Solv = CH3CN (3) and DMF (4)]. All compounds have been fully characterized by 1H and 13C NMR spectroscopy, ESI or FAB mass spectrometry, and elemental analysis. The molecular structures of A and 1-4 have been determined by X-ray single-crystal diffraction. The catalytic activities of 1-4 toward Mizoroki-Heck coupling reactions of aryl bromides with tert-butyl acrylate are described and compared. © 2006 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/219527
ISSN
2015 Impact Factor: 4.186
2015 SCImago Journal Rankings: 2.043

 

DC FieldValueLanguage
dc.contributor.authorYen, Swee Kuan-
dc.contributor.authorKoh, Lip Lin-
dc.contributor.authorHahn, F. Ekkehardt-
dc.contributor.authorHuynh, Han Vinh-
dc.contributor.authorHor, T. S Andy-
dc.date.accessioned2015-09-23T02:57:18Z-
dc.date.available2015-09-23T02:57:18Z-
dc.date.issued2006-
dc.identifier.citationOrganometallics, 2006, v. 25, n. 21, p. 5105-5112-
dc.identifier.issn0276-7333-
dc.identifier.urihttp://hdl.handle.net/10722/219527-
dc.description.abstractUnder solventless conditions, benzothiazole reacts with benzyl bromide to give near-quantitative yield of the salt W-benzylbenzothiazolium bromide (A), which is a convenient air-stable heterocyclic carbene precursor. Treatment of A with Pd(OAc)2 in CH3CN affords the bis(carbene) complex cis-[PdBr2(NHC)2] (1) (NHC = N-benzylbenzothiazolin-2- ylidene). In DMSO, this reaction yields an unprecedented dinuclear N,S-heterocyclic carbene complex, [PdBr2(NHC)]2 (2). Complex 2 undergoes bridge cleavage reactions with CH3CN and DMF to give the mononuclear and solvated monocarbene complexes trans-[PdBr 2(NHC)(Solv)] [Solv = CH3CN (3) and DMF (4)]. All compounds have been fully characterized by 1H and 13C NMR spectroscopy, ESI or FAB mass spectrometry, and elemental analysis. The molecular structures of A and 1-4 have been determined by X-ray single-crystal diffraction. The catalytic activities of 1-4 toward Mizoroki-Heck coupling reactions of aryl bromides with tert-butyl acrylate are described and compared. © 2006 American Chemical Society.-
dc.languageeng-
dc.relation.ispartofOrganometallics-
dc.titleConvenient entry to mono- and dinuclear palladium(II) benzothiazolin-2- ylidene complexes and their activities toward Heck Coupling-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1021/om060510n-
dc.identifier.scopuseid_2-s2.0-33750296864-
dc.identifier.volume25-
dc.identifier.issue21-
dc.identifier.spage5105-
dc.identifier.epage5112-

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