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Article: Convenient entry to mono- and dinuclear palladium(II) benzothiazolin-2- ylidene complexes and their activities toward Heck Coupling
Title | Convenient entry to mono- and dinuclear palladium(II) benzothiazolin-2- ylidene complexes and their activities toward Heck Coupling |
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Authors | |
Issue Date | 2006 |
Citation | Organometallics, 2006, v. 25, n. 21, p. 5105-5112 How to Cite? |
Abstract | Under 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 Identifier | http://hdl.handle.net/10722/219527 |
ISSN | 2023 Impact Factor: 2.5 2023 SCImago Journal Rankings: 0.654 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Yen, Swee Kuan | - |
dc.contributor.author | Koh, Lip Lin | - |
dc.contributor.author | Hahn, F. Ekkehardt | - |
dc.contributor.author | Huynh, Han Vinh | - |
dc.contributor.author | Hor, T. S Andy | - |
dc.date.accessioned | 2015-09-23T02:57:18Z | - |
dc.date.available | 2015-09-23T02:57:18Z | - |
dc.date.issued | 2006 | - |
dc.identifier.citation | Organometallics, 2006, v. 25, n. 21, p. 5105-5112 | - |
dc.identifier.issn | 0276-7333 | - |
dc.identifier.uri | http://hdl.handle.net/10722/219527 | - |
dc.description.abstract | Under 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.language | eng | - |
dc.relation.ispartof | Organometallics | - |
dc.title | Convenient entry to mono- and dinuclear palladium(II) benzothiazolin-2- ylidene complexes and their activities toward Heck Coupling | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/om060510n | - |
dc.identifier.scopus | eid_2-s2.0-33750296864 | - |
dc.identifier.volume | 25 | - |
dc.identifier.issue | 21 | - |
dc.identifier.spage | 5105 | - |
dc.identifier.epage | 5112 | - |
dc.identifier.isi | WOS:000240912400024 | - |
dc.identifier.issnl | 0276-7333 | - |