Rhodium–NHC-complexes as potent catalysts in the hydroformylation of 1-octene

Bortenschlager, Martin; Schütz, Jan; Preysing, Denise von; Nuyken, Oskar; Herrmann, Wolfgang A.; Weberskirch, Ralf

doi:10.1016/j.jorganchem.2005.09.038

Cited by 65 publications

(43 citation statements)

References 29 publications

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“…Complexes 1 – 3 and 1 ox (generated in situ with the addition of the chemical oxidant [AcFc]PF 6 ) were evaluated as catalyst precursors in the hydroformylation of 1‐octene. The cod complexes were employed as catalyst precursors, as the first step in the hydroformylation catalytic cycle is the substitution of the cod moiety by carbonyl ligands . The reaction conditions for 1 were optimized by variation of the syngas pressure (30–50 bar), temperature (55–95 °C), reaction time (4–8 h) and catalyst loading (0.04–0.08 mol‐%) (Table S1).…”

Section: Resultsmentioning

confidence: 99%

A Triarylated 1,2,3‐Triazol‐5‐ylidene Ligand with a Redox‐Active Ferrocenyl Substituent for Rhodium(I)‐Catalyzed Hydroformylation of 1‐Octene

et al. 2017

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A series of rhodium(I)-1,2,3-triazol-5-ylidene (trz) complexes are described, containing either a novel triarylated trz ligand A′ (N1, N3-arylated, C4-ferrocenyl) {complexes 1, [Rh(A′)Cl(cod)]; 4, [Rh(A′)Cl(CO) 2 ]}, or N3-alkylated triazolylidenes with a C4-ferrocenyl {2, [Rh(B′)Cl(cod)]; 5, [Rh(B′)Cl(CO) 2 ]} or C4-phenyl substituent {3, [Rh(C′)Cl(cod)]; 6, [Rh(C′)Cl(CO) 2 ]}. The free mesoionic carbene (MIC) A′ is structurally characterized and its electronic properties evaluated by employing the [a] 1227 Scheme 1. Synthesis of tri -(1, 4) and diarylated (2, 3, 5 and 6) triazolylidene-Rh I complexes.Scheme 2. Synthesis of free carbene A′ and Pd II complex 7. Crystal Structure Determination: Single crystal X-ray diffraction data for A, A ox , 1, 2 and 4 were collected with a Bruker Apex II-CCD detector using Mo-K α radiation (λ = 0.71073 Å), while for A′ Eur.

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Section: Resultsmentioning

confidence: 99%

A Triarylated 1,2,3‐Triazol‐5‐ylidene Ligand with a Redox‐Active Ferrocenyl Substituent for Rhodium(I)‐Catalyzed Hydroformylation of 1‐Octene

et al. 2017

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“…The first metal-NHC complexes were reported in 1968 by Wanzlick and Schönherr [4] and by Öfele [5] and the first stable free carbenes were isolated in 1991 by Arduengo et al [6,7] They form strong bonds to metal centers [8][9][10][11][12] and this makes them particularly beneficial in their use as ligands in organometallic catalysts. Contemporary NHC research is both vigorous and diverse; the chemistry of NHC complexes is the frequently the subject of review articles [13][14][15][16][17][18] and metal-NHC complexes of many transition elements have been reported.…”

Section: Introductionmentioning

confidence: 99%

N‐Heterocyclic Carbene Complexes of Rhodium and Iridium: Steric Effects on Molecular Conformation

Nichol

Rajaseelan²,

Anna

et al. 2009

Eur J Inorg Chem

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A series of new Rh I triazole-based N-heterocyclic carbene (NHC) complexes [(cod)Rh(NHC)Cl] 2a-c were obtained by transmetallation from Ag I complexes using n-butyl, benzyl and neopentyl NHC wing tip substituents. The corresponding new Rh I ionic complexes (3a-c) were synthesized by treating compounds 2a-c with triphenylphosphane and AgBF 4 . These complexes were characterized by nmr spectroscopy and the structures of 2c, 3a, 3b, and 3c were determined by single-crystal X-ray diffraction. Compound 3b formed two polymorphs, the first reported incidence of poly-

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“…Die katalytischen Fähigkeiten von Komplexen mit NHC-Steuerliganden wurde in den letzten zwei Dekaden eingehend untersucht, wobei in der Hydrosilylierung, [88] Olefinmetathese, [14d, 17e, 89] Hydroformylierung, [90] Hydrierung, [91] mannigfaltigen C-C-Kupplungsreaktionen [92] und beim Wasserstofftransfer [93] großes Potential festgestellt wurde. Deshalb ist es nur folgerichtig, die neu synthetisierten wasserlçslichen NHC-Verbindungen auf ihre katalytischen Eigenschaften hin zu untersuchen.…”

Section: Anwendungen Von Metallkomplexen Mit Wasserlçslichen Nhcsunclassified

Synthese und Anwendung wasserlöslicher NHC‐Übergangsmetall‐Komplexe

et al. 2012

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Dieser Aufsatz gibt eine Übersicht über Übergangsmetallkomplexe mit wasserlöslichen NHC‐Liganden. Bekannte Routen zur Einführung von Wasserlöslichkeit durch gezieltes Ligandendesign werden beleuchtet, und einige allgemeine Eigenschaften wasserlöslicher NHC‐Komplexen werden diskutiert. Die erhöhte Hydrophilie wasserlöslicher Katalysatoren bietet zusätzliche Vorteile für Anwendungen in der Synthese. Neben klassischen Umsetzungen, wie z. B. C‐C‐Kupplungen, umfassen neuere Beispiele von Katalysen mit wasserlöslichen NHC‐Komplexen auch Metathesen und Hydrierungen, in denen sich diese Katalysatoren als besonders leistungsfähig erweisen. Insgesamt ist das Gebiet in weiten Teilen noch unerforscht und hat daher ein großes Potenzial für zukünftige Forschung.

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Rhodium–NHC-complexes as potent catalysts in the hydroformylation of 1-octene

Cited by 65 publications

References 29 publications

A Triarylated 1,2,3‐Triazol‐5‐ylidene Ligand with a Redox‐Active Ferrocenyl Substituent for Rhodium(I)‐Catalyzed Hydroformylation of 1‐Octene

A Triarylated 1,2,3‐Triazol‐5‐ylidene Ligand with a Redox‐Active Ferrocenyl Substituent for Rhodium(I)‐Catalyzed Hydroformylation of 1‐Octene

N‐Heterocyclic Carbene Complexes of Rhodium and Iridium: Steric Effects on Molecular Conformation

Synthese und Anwendung wasserlöslicher NHC‐Übergangsmetall‐Komplexe

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