Influence of the para-substitution in bis(arylimino)pyridine iron complexes on the catalytic oligomerization and polymerization of ethylene

Görl, Christian; Alt, Helmut G.

doi:10.1016/j.jorganchem.2007.05.036

Cited by 33 publications

(20 citation statements)

References 52 publications

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“…49 Mp 211–212 °C (oxalate salt). 1 H NMR (400 MHz, CDCl 3 ) δ 8.07 (s, 1H), 7.83–7.94 (m, 4H), 7.56 (d, J = 7.2 Hz, 1H), 7.39 (t, J = 7.2 Hz, 1H), 7.32 (dt, J = 7.6, 1.2 Hz, 1H), 7.02–6.84 (m, 2H), 4.47 (t, J = 7.2 Hz, 2H), 3.96 (s, 2H), 3.85 (s, 3H), 3.09 (br s, 4H), 2.63 (br s, 4H), 2.47 (t, J = 7.2 Hz, 2H), 2.08–2.01(m, 2H), 1.66–1.58 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 152.28, 148.17, 143.95, 143.53, 141.71, 141.37, 141.31, 129.19, 126.91, 126.89, 125.14, 124.53, 122.98, 122.35, 121.01, 120.24, 120.02, 119.42, 118.21, 111.17, 57.80, 55.39, 53.50, 50.68, 50.34, 36.98, 28.40, 23.86; Anal.…”

Section: Experimental Methodsmentioning

confidence: 99%

Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands

Keck

Banala

Slack

et al. 2015

Bioorganic & Medicinal Chemistry

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The dopamine D3 receptor (D3R) is a target of pharmacotherapeutic interest in a variety of neurological disorders including schizophrenia, Parkinson's disease, restless leg syndrome, and drug addiction. A common molecular template used in the development of D3R-selective antagonists and partial agonists incorporates a butylamide linker between two pharmacophores, a phenylpiperazine moiety and an extended aryl ring system. The series of compounds described herein incorporates a change to that chemical template, replacing the amide functional group in the linker chain with a 1,2,3-triazole group. Although the amide linker in the 4-phenylpiperazine class of D3R ligands has been previously deemed critical for high D3R affinity and selectivity, the 1,2,3-triazole moiety serves as a suitable bioisosteric replacement and maintains desired D3R-binding functionality of the compounds. Additionally, using mouse liver microsomes to evaluate CYP450-mediated phase I metabolism, we determined that novel 1,2,3-triazole-containing compounds modestly improves metabolic stability compared to amide-containing analogues. The 1,2,3-triazole moiety allows for the modular attachment of chemical subunit libraries using copper-catalyzed azide-alkyne cycloaddition click chemistry, increasing the range of chemical entities that can be designed, synthesized, and developed toward D3R-selective therapeutic agents.

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Section: Experimental Methodsmentioning

confidence: 99%

Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands

Keck

Banala

Slack

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Methylaluminoxane (MAO 10 wt % in toluene) and TMA (trimethylaluminum) were purchased from Chemtura, while [PhOAlMe 2 ] 2 was obtained by addition of an equimolar amount of phenol to TMA in n-heptane in good yield (97 %) and was characterized by 1 H and 13 C NMR and XRD [27]. [LFe(II)Cl 2 ] was prepared according to the procedure described in ref [28].…”

Section: Methodsmentioning

confidence: 99%

Understanding the role of aluminum-based activators in single site iron catalysts for ethylene oligomerization

Boudene

Boudier

Breuil

et al. 2014

Journal of Catalysis

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In a combined experimental and theoretical study the activation process of a single site ethylene oligomerization catalyst with aluminum based activators has been studied.The results put forward a plausible deactivation reaction path of the catalyst for trimethylaluminum, while for methylaluminoxane and a novel phenoxyaluminum-based activator the experimental catalyst's activity correlates with the energy barrier for the ethylene insertion. Graphical AbstractN N N Fe N N N Fe Al Al Cl TMA MAO or [PhOAlMe 2 ] 2 inactive catalyst oligomerization Cl Cl N N N Fe

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“…The influence of the para-substituent on the N-aryl rings in bis(arylimino)pyridine-iron complexes 4 ( Figure 4) has been studied by the Alt group [59]. In the presence of MAO, the resultant catalysts can oligo-/polymerize ethylene to give highly linear products with the size and the electronegativity of the para-substituents playing an important role in determining activity [59]. (Table 1).…”

Section: < Figure 3>mentioning

confidence: 99%

Carbocyclic-fused N,N,N-pincer ligands as ring-strain adjustable supports for iron and cobalt catalysts in ethylene oligo-/polymerization

Wang

Solan

Zhang

et al. 2018

Coordination Chemistry Reviews

181

101

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Recent progress in the application of homogeneous iron and cobalt catalysts in ethylene oligo-/polymerization is reviewed with particular emphasis placed on the tuning of catalyst performance through the introduction of controlled amounts of ring strain to the ligand frame. While new examples of catalysts bearing the prototypical bis(arylimino)pyridine continue to emerge in the literature, the last decade has witnessed a number of key advances concerned with the fusion of carbocyclic units to the N,N,N-pincer manifold with a view to enhancing both the catalytic activities and thermal stability of their resultant catalysts. Some notable examples include iron complexes containing aryl-fused imino-phenanthroline ligands, which have proved highly active catalysts for ethylene oligomerization and indeed have shown considerable industrial promise on the pilot plant scale. Elsewhere, bis(arylimino)pyridines incorporating singly or doubly fused cycloalkyl units with the ring sizes anywhere between five-and eight-membered have been systematically developed and have proved versatile supports for both metal centers. More significantly, clear correlations between structure and activity as well as oligo-/polymer properties are a feature of these strain-adjustable catalysts. In many cases, linear vinyl-polyethylenes are accessible which are in demand for the production of long-chain branched copolymers, functional polymers as well as coating materials.

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Influence of the para-substitution in bis(arylimino)pyridine iron complexes on the catalytic oligomerization and polymerization of ethylene

Cited by 33 publications

References 52 publications

Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands

Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands

Understanding the role of aluminum-based activators in single site iron catalysts for ethylene oligomerization

Carbocyclic-fused N,N,N-pincer ligands as ring-strain adjustable supports for iron and cobalt catalysts in ethylene oligo-/polymerization

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