Citation:
LU Xue-Chun, LIANG Hong, DENG Jian-Qin, CHENG Xing, CHEN Jian-Xin, ZHANG Zhi-Chun. Synthesis, Structure and Catalytic Activity of a Palladium(II) Complex Based on 4-Chloro-2-[(6-methyl-pyridin-2-ylimino)-methyl]-phenol Ligand[J]. Chinese Journal of Structural Chemistry,
;2016, 35(5): 725-730.
doi:
10.14102/j.cnki.0254-5861.2011-0923
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The title complex bis{4-chloro-2-[(6-methyl-pyridin-2-ylimino)-methyl]-phenol}-palladium(II) (C26H20Cl2N4O2Pd) has been synthesized by the reaction of 4-chloro-2-[(6-methyl-pyridin-2-ylimino)-methyl]-phenol with Pd(CH3COO)2, and characterized by IR spectrum and elemental analysis. Single-crystal X-ray diffraction analysis results further confirmed the molecular structures. The crystal belongs to the monoclinic system, space group P21/c with a = 4.1324(2), b = 23.5432(16), c = 11.8943(8) Å, β = 91.238(5)°, V = 1156.93(12) Å3, C26H20Cl2N4O2Pd, Mr = 597.76, Z = 2, Dc = 1.716 g/cm3, μ = 1.067 mm-1, F(000) = 600, the final R = 0.0247 and wR = 0.0677 (I > 2s(I)). In the presence of methylaluminoxane (MAO), the complex exhibits excellent catalytic activities (1.737×107 g of PNB (mol of Pd)-1×h-1) in the vinyl polymerization of norbornene.
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Keywords:
- nickel complex,
- crystal structure,
- catalyst,
- norbornene polymerization
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[1]
(1) Janiak, C.; Lassahn, P. G. Metal catalysts for the vinyl polymerization of norbornene. J. Mol. Catal. A 2001, 166, 193-209.
-
[2]
(2) Karafilidis, C.; Hermann, H.; Rufinska, A.; Gabor, B.; Mynott, R. J.; Breitenbruch, G.; Weidenthaler, C.; Rust, J.; Joppek, W.; Brookhart, M. S.; Thiel, W.; Fink, G. Metallocene-catalyzed C7-linkage in the hydrooligomerization of norbornene by sigma-bond metathesis: insight into the microstructure of polynorbornene. Angew. Chem. Int. Ed. 2004, 43, 2444-2446.
-
[3]
(3) Karafilidis, C.; Angermund, K.; Gabor, B.; Rufinska, A.; Mynott, R. J.; Breitenbruch, G.; Thiel, W.; Fink, G. Helical microstructure of polynorbornene. Angew. Chem. Int. Ed. 2007, 46, 3745-3749.
-
[4]
(4) Moulton, B.; Zaworotko, M. J. From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. Chem. Rev. 2001, 101, 1629-1658.
-
[5]
(5) Evans, O. R.; Lin, W. B. Crystal engineering of nlo materials based on metal-organic coordination networks. Acc. Chem. Res. 2002, 35, 511-522.
-
[6]
(6) Carlucci, L.; Ciani, G.; Proserpio, D. M. Polycatenation, polythreading and polyknotting in coordination network chemistry. Chem. Rev. 2003, 246, 247-289.
-
[7]
(7) Batten, S. R.; Champness, N. R.; Chen, X. M.; Garcia-Martinez, J.; Kitagawa, S.; Ohrstrom, L.; O'Keeffe, M.; Suh, M. P.; Reedijk, J. Terminology of metal-organic frameworks and coordination polymers (IUPAC recommendations 2013). Pure Appl. Chem. 2013, 85, 1715-1724.
-
[8]
(8) Ito, S.; Nozaki, K. Coordination-insertion copolymerization of polar vinyl monomers by palladium catalysts. Chem. Rec. 2010, 10, 315-325.
-
[9]
(9) Nakamura, A.; Anselment, T. M. J.; Claverie, J.; Goodall, B.; Jordan, R. F.; Mecking, S.; Rieger, B.; Sen, A. Van Leeuwen, P. W. N. M.; Nozaki, K. ortho-phosphinobenzenesulfonate: a superb ligand for palladium-catalyzed coordination-insertion copolymerization of polar vinyl monomers. Acc. Chem. Res. 2013, 46, 1438-1449.
-
[10]
(10) Nomura, H.; Richards, C. J. Allylic imidate rearrangements catalyzed by planar chiral palladacycles. Chem. Asian. J. 2010, 5, 1726-1740.
-
[11]
(11) Alonso, D. A.; Najera, C. Oxime-derived palladacycles as source of palladium nanoparticles. Chem. Soc. Rev. 2010, 39, 2891-2902.
-
[12]
(12) Wu, Y. J.; Yang, F.; Zhang, J. L.; Cui, X. L.; Gong, J. F.; Song, M. P.; Li, T. S. Cyclopalladated ferrocenylimines as efficient catalysts for homogeneous catalysis: a brief introduction to our preliminary achievements. Chin. Sci. Bull. 2010, 55, 2784-2793.
-
[13]
(13) Kong, Y.; Wen, L. F.; Song, H. B.; Xu, S. S.; Yang, M.; Liu, B. Y.; Wang, B. Q. Synthesis, structures, and norbornene polymerization behavior of aryloxide-N-heterocyclic carbene ligated palladacycles. Organometallics 2011, 30, 153-159.
-
[14]
(14) Gui, G. Q.; Bao, F.; Gao, H. Y.; Zhu, F. M.; Wu, Q. Vinyl polymerization of norbornene catalyzed by a new bis(β-ketoamino)nickel(II) complex-methylaluminoxane system. Appl. Organometal. Chem. 2005, 19, 627-632.
-
[15]
(15) Liang, H.; Liu, J. Y.; Li, X. F.; Li, Y. S. Synthesis, structure and norbornene polymerization behavior of neutral palladium complexes. Polyhedron 2004, 23, 1619-1627.
-
[16]
(16) Zhang, D.; Zhou, S.; Li, Z. M.; Wang, Q. R.; Weng, L. H. Direct synthesis of cis-dihalido-bis(NHC) complex of nickel(II) and catalytic application in olefin addition polymerization: effect of halogen co-ligands and density functional theory study. Dalton Trans. 2013, 42, 12020-12030.
-
[17]
(17) Deng, J. A.; Gao, H. Y.; Zhu, F. M.; Wu, Q. Synthesis and structure of imine-N-heterocyclic carbene palladium complexes and their catalytic behavior in norbornene polymerization. Organometallics 2013, 32, 4507-4515.
-
[18]
(18) Budagumpi, S.; Haque, R. A.; Salman, A. W. Stereochemical and structural characteristics of single-and double-site Pd(II)-N-heterocyclic carbene complexes: promising catalysts in organic syntheses ranging from C-C coupling to olefin polymerizations. Coord. Chem. Rev. 2012, 256, 1787-1830.
-
[19]
(19) Dang, L.; Song, H. B.; Wang, B. Q. Synthesis, structures, and norbornene polymerization behavior of o-aryloxide-substituted NHC-ligated sigma, pi-cycloalkenyl palladium complexes. Chemistry, Organic 2014, 33, 6812-6818.
-
[20]
(20) Long, J. M.; Gao, H. Y.; Song, K. M.; Liu, F. S.; Hu, H.; Zhang, L.; Zhu, F. M.; Wu, Q. Synthesis and characterization of Ni II and Pd II complexes bearing N,N,S tridentate ligands and their catalytic properties for norbornene polymerization. Eur. J. Inorg. Chem. 2008, 4296-4305.
-
[21]
(21) Li, C.; Meng, S. Q.; Lan, M. Y.; Yu, Y. H.; Chen, J. X.; Zhang, Z. C. Synthesis, structure and norbornene polymerization catalyzed by bis{1-[[(3-ethyl-6-methyl-2-pyridinyl)imino]methylenyl]-2-naphthalenolato-N,O}nickel(II). Chin. J. Struct. Chem. 2014, 33, 289-293.
-
[22]
(22) Haselwander, T. F. A.; Heitz, W. Vinylic polymerization of norbornene by Pd(II)-catalysis in the presence of ethylene. Macromol. Rapid Commun. 1997, 18, 689-697.
-
[23]
(23) Hou, J. X.; Sun, W. H.; Zhang, D. H.; Chen, L. Y.; Li, W.; Zhao, D. F.; Song, H. B. Preparation and characterization of acylhydrazone nickel(II) complexes and their catalytic behavior in vinyl polymerization of norbornene and oligomerization of ethylene. J. Mol. Catal. A: Chem. 2005, 231, 221-233.
-
[24]
(24) Zhao, C. T.; do Rosário Ribeiro, M.; De Pinho, M. N.; Subrahmanyam, V. S.; Gil, C. L.; de Lima, A. P. Structural characteristics and gas permeation properties of polynorbornenes with retained bicyclic structure. Polymer 2001, 42, 2455-2462.
-
[25]
(25) Haselwander, T. F. A.; Heitz, W.; Krügel, S. A.; Wendorff, J. H. Polynorbornene: synthesis, properties and simulations. Macromol. Chem. Phys. 1996, 197, 3435-3453.
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