Cyclopalladated complexes derivates of phenylhydrazones and their use as catalysts in ethylene polymerization

Pérez, Mónica A.; Quijada, Raúl; Ortega-Jiménez, Fernando; Álvarez-Toledano, Cecilio

doi:10.1016/j.molcata.2004.08.013

Cited by 15 publications

(10 citation statements)

References 22 publications

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“…Complex 1 shows high activity, in accord with values normally obtained for nonmetallocene complexes [16]. This activity is similar to that obtained by Perez et al [17] for related cyclopalladate complexes derived from phenylhydrazones (C, N, N-donor). For these compounds, which have a single chloride, UV-visible spectroscopy supports the formation of successive steps in the polymerization reaction with formation of cationic species.…”

Section: Ethylene Polymerization Activitiessupporting

confidence: 89%

Synthesis, characterization, and reactivity studies in ethylene polymerization of cyclometalated palladium(II) complexes containing terdentate ligands with N,C,N-donors

Hurtado

Portaluppi

Quijada

et al. 2009

Journal of Coordination Chemistry

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Section: Ethylene Polymerization Activitiessupporting

confidence: 89%

Synthesis, characterization, and reactivity studies in ethylene polymerization of cyclometalated palladium(II) complexes containing terdentate ligands with N,C,N-donors

Hurtado

Portaluppi

Quijada

et al. 2009

Journal of Coordination Chemistry

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“…For example emine-type cyclopalladated products 2.14 have good activity for ethylene polymerization [101]. The molecular weight and molecular weight distribution of the obtained polymers correspond to single-site catalysts, and the polymers have narrow molecular weight distribution, as shown in Table 1.…”

Section: (221)mentioning

confidence: 92%

“…Molecular weight, molecular weight distribution and melting temperature (Tm) of polyethylene obtained using the imine cyclometalated palladium catalysts 2.14b and 2.14c[101].…”

mentioning

confidence: 99%

Applications of Cyclometalation Five-Membered Ring Products and Intermediates as Catalytic Agents

Omae¹

2016

MRC

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The five-membered ring products and intermediates of cyclometalation reactions are very easily synthesized via donation from a hetero atom to a metal atom, which leads to the very high functionality of the product. This functionality is caused by the donation of the hetero atom and various types of metal atoms, halogen atom and other ligands such as alkanes, alkenes, alkynes, Cp, Cp*, aryl groups and heterocyclic compounds. These products have three types of catalytic applications: cyclometalation five-membered ring products as catalysts, cyclometalation five-membered ring intermediates as catalyst agents and cyclometalation five-membered ring intermediates with unconventional substrates and as catalyst actions. Because of the high functionality of these products, the applications of them have been increasing not only as the metathesis in the first and second generations of Hoveyda-Grubbs catalysts but also as in chiral reactions, crosscoupling reactions and polymerization reactions. The above cyclometalation products have been utilized for the production in many industrial fields such as pharmaceuticals, OLEDs, carbon dioxide utilizations, dye-sensitizer solar cells and sensors. We expect that these products would be used for the development of further new industrial products.

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“…23 Due to the modest activity found for this complex we evaluated the catalytic activity only at 60 ºC. We suggest that the polymerization reaction catalyzed by 4 occurs by a mechanism similar to those proposed for square-planar cyclopalladate complexes derived from phenylhydrazones (C,N,N-donor), 31 where the first step is the replacement of the halide by a methyl group, increasing the electron density of the metal atom, followed by cleavage of the M-N bond to generate a vacancy at the metal center (Scheme 3). The lower activity of this complex compared with the similar palladium compound is probably due to the shorter metal-nitrogen bond distances expected for a first row transition metal complex compared with the related second row complex.…”

Section: Resultsmentioning

confidence: 99%

Organonickel(II) complexes with anionic tridentate 1, 3-bis(azolylmethyl)phenyl ligands. synthesis, structural characterization and catalytic behavior

Hurtado¹,

Ibáñez²,

Rojas³

et al. 2011

J. Braz. Chem. Soc.

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A reação de 2-bromo-1,3-bis(bromometil)benzeno com 3,5-dimetilpirazol e 1H-indazol produz os ligantes tridentados 2-bromo-1,3-bis(3,5-dimetilpirazol-1-ilmetil)benzeno (1) e 2-bromo-1,3-bis(indazol-2-ilmetil)benzeno (2). Estes compostos reagem com [Ni(cod) 2 ] em tetraidrofurano (thf) para formar os complexos de adição oxidativa [NiBr{1,3-bis(azolilmetil)fenil-N,C,N}], azol = 3,5-dimetilpirazol (3) e indazol (4), os quais foram isolados em bons rendimentos como sólidos amarelos estáveis e caracterizados por meio de análise elementar, espectroscopia de absorção no infravermelho com transformada de Fourier (FTIR), espectrometria de massa e ressonância magnética nuclear (NMR). Adicionalmente, as estruturas moleculares de 2 e 4 foram determinadas por difratometria de raios X de monocristal. O complexo 4 foi testado como catalisador na reação de polimerização de etileno.The reaction of 2-bromo-1,3-bis(bromomethyl)benzene with 3,5-dimethylpyrazole and 1H-indazole yields the tridentate ligands 2-bromo-1,3-bis(3,5-dimethylpirazol-1-ylmethyl)benzene (1) and 2-bromo-1,3-bis(indazol-2-ylmethyl)benzene (2). These compounds react with [Ni(cod) 2 ] in tetrahydrofuran (thf) to form the oxidative addition complexes [NiBr{1,3-bis(azolylmethyl)phenyl-N,C,N}], azol = 3,5-dimethylpyrazol (3), indazol (4), which were isolated in good yields as stable yellow solids and characterized by elemental analysis, Fourier-transform infrared spectroscopy (FTIR), mass spectroscopy and nuclear magnetic resonance (NMR). In addition, the molecular structures of 2 and 4 were determined by single-crystal X-ray diffraction analysis. Complex 4 was tested as a catalyst in ethylene polymerization reaction.

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Cyclopalladated complexes derivates of phenylhydrazones and their use as catalysts in ethylene polymerization

Cited by 15 publications

References 22 publications

Synthesis, characterization, and reactivity studies in ethylene polymerization of cyclometalated palladium(II) complexes containing terdentate ligands with N,C,N-donors

Synthesis, characterization, and reactivity studies in ethylene polymerization of cyclometalated palladium(II) complexes containing terdentate ligands with N,C,N-donors

Applications of Cyclometalation Five-Membered Ring Products and Intermediates as Catalytic Agents

Organonickel(II) complexes with anionic tridentate 1, 3-bis(azolylmethyl)phenyl ligands. synthesis, structural characterization and catalytic behavior

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