Bi- and trinuclear oxalamidinate complexes of palladium as catalysts in the copper-free Sonogashira reaction and in the Negishi reaction

Rau, Sven; Lamm, Katja; Görls, Helmar; Schöffel, Julia; Walther, Dirk

doi:10.1016/j.jorganchem.2004.07.061

Cited by 47 publications

(27 citation statements)

References 42 publications

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“…A higher degree of delocalisation could be obtained by introduction of alkyne substituents like tri(isopropyl)silylacetylene. [29] In this case, the MLCT absorption of [Ru(tbbpy) 2 The lifetimes of the excited states of all complexes in aerated solution lie in the expected range. Generally, longer lifetimes are identified in aerated dichloromethane solutions if compared with those in aerated acetonitrile solutions.…”

Section: Electronic Spectramentioning

confidence: 84%

“…Preliminary investigations showed that the tetraalkynyl-substituted phenanthrolines may serve as ligands for ruthenium(II) centres. [29] It is noteworthy that the introduction of alkynyl functional groups in bipyridine or phenanthroline frames leads to the expansion of the conjugated π-system which will have a dramatic impact on the metal-to-ligand charge-transfer excited state of ruthenium complexes. The introduction of aryl substituents, however, does not necessarily lead to the expansion of the conjugated π-system since the torsion angle of these substituents relative to the phenanthroline main frame can be substantial, thus limiting delocalisation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of Tetrasubstituted 1,10‐Phenanthrolines and Their Ruthenium Complexes

et al. 2007

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The synthesis and the photophysical properties of a series of tetrasubstituted phenanthroline (phen) ruthenium complexes of the type [Ru(tbbpy) 2 (phen-R 4 )] 2+ (tbbpy = 4,4Ј-di-tert-butyl-2,2Ј-bipyridine; phen = 1,10-phenanthroline; R represents the substitution at 3-, 5-, 6-and 8-positions with phenyl, 4-tert-butylphenyl and para-biphenyl) and of a homoleptic [Ru(phen-RЈ 4 ) 3 ] 2+ (RЈ = 4-tert-butylphenyl) are described. The phen-R 4 ligands were obtained in high yields using Suzuki-type coupling reactions. The solid-state structure of

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Section: Electronic Spectramentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Tetrasubstituted 1,10‐Phenanthrolines and Their Ruthenium Complexes

et al. 2007

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“…Absorption spectra of RuL1 (solid), RuL2 (dashed), RuL3 (dotted) and RuL4 (dash-dotted) in dichloromethane; an enlargement of the MLCT region is depicted in the inset. [41] and 497 nm, [42] respectively. The emission maxima and emission lifetimes of complexes RuL1-RuL4 dissolved in dichloromethane were also investigated (Table 3).…”

Section: Electronic Propertiesmentioning

confidence: 99%

Synthesis and Photophysical Properties of 3,8‐Disubstituted 1,10‐Phenanthrolines and Their Ruthenium(II) Complexes

et al. 2009

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The palladium-catalysed cross-coupling reaction between 3,8-dibromo-1,10-phenanthroline with phenylacetylene or 3,5-bis(trifluoromethyl)phenylboronic acid gives good yields of the 3,8-disubstituted products. These 1,10-phenanthroline derivatives are used for the formation of novel ruthenium complexes of the type [(tbbpy) 2 Ru(phenR 2 )] 2+ [where tbbpy = 4,4Ј-di-tert-butyl-2,2Ј-bipyridine, phen = 1,10-phenanthroline, R represents the substituents at the 3,8 positions with bromine, phenylacetylene or 3,5-bis(trifluoromethyl)-phenyl]. All compounds are completely characterised by NMR and UV/Vis spectroscopy, MS, electrochemical measurements and Raman and resonance Raman spectroscopy.

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“…[59] Ein Palladium-Tetraphenyloxalamidinat-Zweikernkomplex wurde als Präkatalysator bei der kupferfreien Sonogashira-Reaktion zwischen 4-Bromacetophenon und Phenylacetylen eingesetzt und ergab mittlere TONs (Schema 27). [60] Yoshifuji et al berichteten über die Verwendung zweizähniger P,P- [61] und P,S-Liganden [62] [67] Das Tedicyp/Palladium-System bildete ferner einen geeigneten Katalysator zur Kreuzkupplung von verschiedenen Heteroarylhalogeniden und Alkinen. [68] Heteroarene wie Pyridin-, Chinolin-und Indol-oder Thiophenderivate ergaben die alkinylierten Addukte in guten Ausbeuten.…”

Section: Systeme Mit Carbenligandenunclassified

Palladium‐Katalysatorsysteme für die Synthese von konjugierten Eninen durch Sonogashira‐Kupplungen und verwandte Alkinylierungen

2007

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Konjugierte Alkine sind stets wiederkehrende Synthesebausteine in Naturstoffen, zahlreichen unverzichtbaren industriellen Zwischenstufen, in Pharmazeutika und Agrochemikalien sowie in molekularen Materialien für Optik und Elektronik. Daher zählt die palladiumkatalysierte Verknüpfung der sp2‐hybridisierten Kohlenstoffatome von Aryl‐, Heteroaryl‐ und Vinylhalogeniden mit den sp‐hybridisierten Kohlenstoffatomen von terminalen Acetylenen in einer Kreuzkupplung unbestreitbar zu den bedeutendsten Entwicklungen der Alkinchemie in den vergangenen fünfzig Jahren. Auf die grundlegenden Arbeiten der 1970er folgte eine intensive Suche nach allgemeineren und verlässlicheren Reaktionsbedingungen. Das Interesse an einer katalytischen Aktivierung anspruchsvoller Substrate, die unbedingte Notwendigkeit, den Ressourcenverbrauch zu minimieren, und die einfache Synthese einer stetig wachsenden Zahl an funktionalisierten Eninen führte allmählich zu den aktuellen Katalysatoren mit hohen Umsatzzahlen. Der vorliegende Aufsatz gibt einen Überblick über hoch wirksame Palladium‐Katalysatorsysteme für die direkte Alkinylierung von C(sp2)‐Halogeniden mit terminalen Alkinen in homogener oder heterogener Phase.

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Bi- and trinuclear oxalamidinate complexes of palladium as catalysts in the copper-free Sonogashira reaction and in the Negishi reaction

Cited by 47 publications

References 42 publications

Synthesis and Properties of Tetrasubstituted 1,10‐Phenanthrolines and Their Ruthenium Complexes

Synthesis and Properties of Tetrasubstituted 1,10‐Phenanthrolines and Their Ruthenium Complexes

Synthesis and Photophysical Properties of 3,8‐Disubstituted 1,10‐Phenanthrolines and Their Ruthenium(II) Complexes

Palladium‐Katalysatorsysteme für die Synthese von konjugierten Eninen durch Sonogashira‐Kupplungen und verwandte Alkinylierungen

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