Palladium-Catalyzed Ethylene/Methyl Acrylate Cooligomerization: Effect of a New Nonsymmetric α-Diimine

被引：55

作者：

Meduri, Angelo ^{[1
]}

Montini, Tiziano ^{[1
]}

Ragaini, Fabio ^{[2
]}

Fornasiero, Paolo ^{[1
]}

Zangrando, Ennio ^{[1
]}

Milani, Barbara ^{[1
]}

机构：

[1] Univ Trieste, Dept Chem & Pharmaceut Sci, I-34127 Trieste, Italy

[2] Univ Milan, Dept Chem, I-20133 Milan, Italy

来源：

CHEMCATCHEM | 2013年 / 5卷 / 05期

关键词：

ethylene; N ligands; oligomerization; palladium; polar monomer; PYRIDINE-IMIDAZOLINE LIGANDS; BIDENTATE NITROGEN LIGANDS; NUCLEAR-MAGNETIC-RESONANCE; RAY CRYSTAL-STRUCTURES; POLAR VINYL MONOMERS; LATE-METAL-CATALYSTS; C-13 NMR ANALYSIS; BIAN LIGANDS; INSERTION POLYMERIZATION; FUNCTIONAL POLYOLEFINS;

D O I：

10.1002/cctc.201200520

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new nonsymmetric bis(aryl-imino)acenaphthene (Ar-BIAN) ligand, featured by a subtle steric and electronic unbalance of the N-donor atoms, is reported. With the new ligand and the corresponding symmetrically substituted derivatives, both neutral and monocationic PdCH3 compounds have been synthesized and characterized. The series of the monocationic complexes [Pd(CH3)(L)(Ar-BIAN)][PF6] (L=CH3CN, dmso) has been extended to dimethyl sulfoxide derivatives. The monocationic complexes are tested as precatalysts for the ethylene/methyl acrylate cooligomerization under mild reaction conditions of temperature and ethylene pressure. The catalytic product is a mixture of ethylene/acrylate cooligomers and higher alkenes. The catalysts containing the new nonsymmetric ligand are found to be more productive than those with the symmetric Ar-BIANs. The Pddmso catalysts are more productive and show a longer lifetime than their PdNCCH3 counterparts.

引用

页码：1170 / 1183

页数：14

共 59 条

[41] Coordination-Insertion Copolymerization of Fundamental Polar Monomers [J].

Nakamura, Akifumi ;

Ito, Shingo ;

Nozaki, Kyoko .

CHEMICAL REVIEWS, 2009, 109 (11) :5215-5244

[42] Limits of Activity: Weakly Coordinating Ligands in Arylphosphinesulfonato Palladium(II) Polymerization Catalysts [J].

Neuwald, Boris ;

Oelscher, Franz ;

Goettker-Schnetmann, Inigo ;

Mecking, Stefan .

ORGANOMETALLICS, 2012, 31 (08) :3128-3137

[43] Efficient incorporation of polar comonomers in copolymerizations with ethylene using a cyclophane-based Pd(II) α-diimine catalyst [J].

Popeney, Christopher S. ;

Camacho, Drexel H. ;

Guan, Zhibin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (33) :10062-+

[44] A new bis(1-naphthylimino)acenaphthene compound and its Pd(II) and Zn(II) complexes:: Synthesis, characterization, solid-state structures and density functional theory studies on the syn and anti isomers [J].

Rosa, Vitor ;

Aviles, Teresa ;

Aullon, Gabriel ;

Covelo, Berta ;

Lodeiro, Carlos .

INORGANIC CHEMISTRY, 2008, 47 (17) :7734-7744

[45] Reactivity of Methacrylates in Insertion Polymerization [J].

Ruenzi, Thomas ;

Guironnet, Damien ;

Goettker-Schnetmann, Inigo ;

Mecking, Stefan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) :16623-16630

[46] NMR-STUDY ON THE COORDINATION BEHAVIOR OF DISSYMMETRIC TERDENTATE TRINITROGEN LIGANDS ON METHYLPALLADIUM(II) COMPOUNDS [J].

RULKE, RE ;

ERNSTING, JM ;

SPEK, AL ;

ELSEVIER, CJ ;

VANLEEUWEN, PWNM ;

VRIEZE, K .

INORGANIC CHEMISTRY, 1993, 32 (25) :5769-5778

[47] Trifluoroethanol: Key solvent for palladium-catalyzed polymerization reactions [J].

Scarel, A ;

Durand, J ;

Franchi, D ;

Zangrando, E ;

Mestroni, G ;

Milani, B ;

Gladiali, S ;

Carfagna, C ;

Binotti, B ;

Bronco, S ;

Gragnoli, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (08) :2106-2120

[48] Subtle balance of steric and electronic effects for the synthesis of atactic polyketones catalyzed by Pd complexes with meta-substituted aryl-BIAN ligands [J].

Scarel, Alessandro ;

Axet, M. Rosa ;

Amoroso, Francesco ;

Ragaini, Fabio ;

Elsevier, Cornelis J. ;

Holuigue, Alexandre ;

Carfagna, Carla ;

Mosca, Luca ;

Milani, Barbara .

ORGANOMETALLICS, 2008, 27 (07) :1486-1494

[49] Perspective on metal-mediated polar monomer/alkene copolymerization [J].

Sen, Ayusman ;

Borkar, Sachin .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (15) :3291-3299

[50] Synthesis of Hyperbranched Polyethylene Amphiphiles by Chain Walking Polymerization in Tandem with RAFT Polymerization and Supramolecular Self-Assembly Vesicles [J].

Shi, Xinbo ;

Zhao, Ye ;

Gao, Haiyang ;

Zhang, Ling ;

Zhu, Fangming ;

Wu, Qing .

MACROMOLECULAR RAPID COMMUNICATIONS, 2012, 33 (05) :374-379

← 1 2 3 4 5 6 →