2013
DOI: 10.1021/om400268y
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Synthesis and Structure of Imine–N-Heterocyclic Carbene Palladium Complexes and Their Catalytic Behavior in Norbornene Polymerization

Abstract: On the basis of the steric effects of ligand, a series of imine–N-heterocyclic carbene (NHC) ligands and their corresponding five-membered palladium complexes with bulky substituents on both the imine and the NHC moieties were synthesized and characterized. Transpalladation of silver carbene complexes with (COD)­PdCl2 and (COD)­PdMeCl afforded the palladium dichloride and methylpalladium complexes, respectively. Bulky cationic palladium complexes were further obtained by treatment of the methylpalladium comple… Show more

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Cited by 53 publications
(26 citation statements)
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References 87 publications
(40 reference statements)
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“…The intermediate products N ‐(2,6‐diisopropylphenyl)acetamide, N ‐(2,6‐dimethylphenyl)acetamide, N ‐phenylbenzamide, N ‐(2,6‐dimethylphenyl)benzamide, N ‐(2,6‐dimethylphenyl)acetimidoyl chloride, N ‐(2,6‐diisopropylphenyl)acetimidoyl chloride, N ‐(2,6‐dimethylphenyl)benzenecarboximidoyl chloride, and N ‐phenylbenzenecarboximidoyl chloride were prepared according to previously reported procedures . The imine‐N‐heterocyclic carbene ligands L1–L4 , L5 , L6–L9 , and L10 were prepared according to slightly modified procedures reported previously. For the biological experiments, Dulbecco′s Modified Eagle′s Medium (DMEM), fetal bovine serum, penicillin/streptomycin mixture, trypsin/EDTA, phosphate‐buffered saline (PBS), MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide), PI (propidium iodide), JC‐1 (5,5′,6,6′‐tetrachloro‐1,1′,3,3′‐tetraethylbenzimidazolyl carbocyanine iodide), and H 2 DCFDA (2′,7′‐dichlorodihydrofluorescein diacetate) were purchased from Sangon Biotech.…”
Section: Methodsmentioning
confidence: 95%
“…The intermediate products N ‐(2,6‐diisopropylphenyl)acetamide, N ‐(2,6‐dimethylphenyl)acetamide, N ‐phenylbenzamide, N ‐(2,6‐dimethylphenyl)benzamide, N ‐(2,6‐dimethylphenyl)acetimidoyl chloride, N ‐(2,6‐diisopropylphenyl)acetimidoyl chloride, N ‐(2,6‐dimethylphenyl)benzenecarboximidoyl chloride, and N ‐phenylbenzenecarboximidoyl chloride were prepared according to previously reported procedures . The imine‐N‐heterocyclic carbene ligands L1–L4 , L5 , L6–L9 , and L10 were prepared according to slightly modified procedures reported previously. For the biological experiments, Dulbecco′s Modified Eagle′s Medium (DMEM), fetal bovine serum, penicillin/streptomycin mixture, trypsin/EDTA, phosphate‐buffered saline (PBS), MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide), PI (propidium iodide), JC‐1 (5,5′,6,6′‐tetrachloro‐1,1′,3,3′‐tetraethylbenzimidazolyl carbocyanine iodide), and H 2 DCFDA (2′,7′‐dichlorodihydrofluorescein diacetate) were purchased from Sangon Biotech.…”
Section: Methodsmentioning
confidence: 95%
“…The vinyl type polymers of norbornene are important for its dielectric property and are used in microelectronics applications [305] (Scheme 52). The complexes (341), [124] (360), [306] (548), [306] (557), [306] (570−573), [174] (574), [175] (622−623), [306] (677) [204] and (785) [175] catalyzed norbornene polymerization in the presence of MAO.…”
Section: Norbornene Polymerizationmentioning
confidence: 99%
“…The reduced oxophilicity of late transition metal palladium(II) complexes endows the catalysts with the ability to produce copolymers with a variety of polar‐functionalized olefins, allowing the preparation of complex functional polymer architectures. Much significant work has been done by many researchers with palladium(II)‐based systems for the vinyl‐type addition polymerization of a wide variety of NB derivatives under mild conditions . Additionally, copolymerization of NB with 5‐NB‐2‐carboxylic acid methyl ester in toluene using the (Cp)Ni(Cl)(PPh 3 )/AlMe 3 /B(C 6 F 5 ) 3 system has been achieved in moderate yields (up to 68% in 2 h at room temperature) .…”
Section: Introductionmentioning
confidence: 99%