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Article: Benzimidazolium-pyrazole-palladium(II) complexes: New and efficient catalysts for Suzuki, Heck and Sonogashira reactions

TitleBenzimidazolium-pyrazole-palladium(II) complexes: New and efficient catalysts for Suzuki, Heck and Sonogashira reactions
Authors
KeywordsWater channel
N-heterocyclic carbenes
Palladium
X-ray structure determination
Cross-coupling
Hybrid ligands
Issue Date2008
Citation
Advanced Synthesis and Catalysis, 2008, v. 350, n. 14-15, p. 2391-2400 How to Cite?
AbstractThree unsymmetrical benzimidazoliumpyrazole N-N ligands 2-(1-propylbenzimidazolylmethyl)-3,5-di-R-pyrazole (R=H, Me, t-Bu) have been conveniently prepared and structurally analyzed. The solid lattice packingof the R=Me compound at 223 K reveals one-dimensional "zig-zag" water chains stabilized by organic molecular channels through N⋯H-O and O-H⋯O bonding. These hybrid ligands add to palladium(II) to give high yields of air-stable complexes that are fully characterized by NMR, ESI, and X-ray single-crystal crystallography. They are active Suzuki catalysts at room temperature towards cross-couplingof unactivated aryl bromides and 5- or 6-membered heteroaryl bromides with arylboronic acids with turnover frequencies (TOF) reachingas high as 60,000 h-1. Their catalytic efficiency is significantly better than that of the C-N carbene-imidazole analogue. These catalysts are also active in Heck and Sonogashira cross-coupling reactions of aryl bromides giving the desired products in good yields. These results suggested that these Pd(II) complexes with N-based hybrid ligands are versatile and efficient catalysts for different types of cross-couplingreactio ns under aerobic conditions. © 2008 Wiley-VCH VerlagGmbH & Co. KGaA.
Persistent Identifierhttp://hdl.handle.net/10722/219821
ISSN
2015 Impact Factor: 6.453
2015 SCImago Journal Rankings: 2.729

 

DC FieldValueLanguage
dc.contributor.authorLi, Fuwei-
dc.contributor.authorHor, T. S Andy-
dc.date.accessioned2015-09-23T02:58:02Z-
dc.date.available2015-09-23T02:58:02Z-
dc.date.issued2008-
dc.identifier.citationAdvanced Synthesis and Catalysis, 2008, v. 350, n. 14-15, p. 2391-2400-
dc.identifier.issn1615-4150-
dc.identifier.urihttp://hdl.handle.net/10722/219821-
dc.description.abstractThree unsymmetrical benzimidazoliumpyrazole N-N ligands 2-(1-propylbenzimidazolylmethyl)-3,5-di-R-pyrazole (R=H, Me, t-Bu) have been conveniently prepared and structurally analyzed. The solid lattice packingof the R=Me compound at 223 K reveals one-dimensional "zig-zag" water chains stabilized by organic molecular channels through N⋯H-O and O-H⋯O bonding. These hybrid ligands add to palladium(II) to give high yields of air-stable complexes that are fully characterized by NMR, ESI, and X-ray single-crystal crystallography. They are active Suzuki catalysts at room temperature towards cross-couplingof unactivated aryl bromides and 5- or 6-membered heteroaryl bromides with arylboronic acids with turnover frequencies (TOF) reachingas high as 60,000 h-1. Their catalytic efficiency is significantly better than that of the C-N carbene-imidazole analogue. These catalysts are also active in Heck and Sonogashira cross-coupling reactions of aryl bromides giving the desired products in good yields. These results suggested that these Pd(II) complexes with N-based hybrid ligands are versatile and efficient catalysts for different types of cross-couplingreactio ns under aerobic conditions. © 2008 Wiley-VCH VerlagGmbH & Co. KGaA.-
dc.languageeng-
dc.relation.ispartofAdvanced Synthesis and Catalysis-
dc.subjectWater channel-
dc.subjectN-heterocyclic carbenes-
dc.subjectPalladium-
dc.subjectX-ray structure determination-
dc.subjectCross-coupling-
dc.subjectHybrid ligands-
dc.titleBenzimidazolium-pyrazole-palladium(II) complexes: New and efficient catalysts for Suzuki, Heck and Sonogashira reactions-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1002/adsc.200800356-
dc.identifier.scopuseid_2-s2.0-55049140516-
dc.identifier.volume350-
dc.identifier.issue14-15-
dc.identifier.spage2391-
dc.identifier.epage2400-
dc.identifier.eissn1521-3897-

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