A series of nickel complexes [Ni(L1)Br2] (C1), [Ni(L2)Br2] (C2) and [Ni(L3)Br2] (C3) (L1 = N-isopropyl-N-(((diphenylphosphanyl)methyl)dimethylsilyl)-1,1-diphenylphosphanamine, L2 = N-cyclopentyl-N-(((diphenylphosphanyl)methyl)dimethylsilyl)-1,1-diphenylphosphanamine, L3 = N-(2,6-diisopropylphenyl)-N-(((diphenylphosphanyl)methyl)dimethylsilyl)-1,1-diphenylphosphanamine) were synthesized and characterized by elemental analysis, mass spectrometry, spectroscopy and single-crystal X-ray diffraction. L1, L2 and L3 each act as bidentate ligands. Upon activation with ethylaluminum dichloride, these complexes produce efficient catalytic systems for selective dimerization of ethylene to 1-butene, with catalytic activities of 3.45 × 107 g/(molNi·h) and 95.6% butene selectivity containing 87.6% 1-butene fraction.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
Wang J, Zhang N, Li CQ, Shi WG, Lin ZY (2016) Nickel complexes based on hyperbranched salicylaldimine ligands: synthesis, characterization, and catalytic properties for ethylene oligomerization. J Organomet Chem 822:104–111
Boulens P, Pellier E, Jeanneau E, Reek JNH, Olivier-Bourbigou H, Breuil P-AR (2015) Self-assembled organometallic nickel complexes as catalysts for selective dimerization of ethylene into 1-butene. Organomet 34(7):1139–1142
Chen H-P, Liu Y-H, Peng S-M, Liu S-T (2003) New bulky phosphino–pyridine ligands. Palladium and nickel complexes for the catalytic polymerization and oligomerization of ethylene. Organomet 22(24):4893–4899
Ngcobo M, Ojwach SO (2017) Nickel(II) complexes chelated by N,N (benzimidazolylmethyl)amine ligands: synthesis and catalytic behavior in tandem ethylene oligomerization and Friedel–Crafts alkylation reactions. Inorg Chim Acta 467:400–404
Popeney CS, Rheingold AL, Guan Z (2009) Nickel(II) and palladium(II) polymerization catalysts bearing a fluorinated cyclophane ligand: stabilization of the reactive intermediate. Organomet 28(15):4452–4463
Speiser F, Braunstein P, Saussine L (2004) New nickel ethylene oligomerization catalysts bearing bidentate P,N-phosphinopyridine ligands with different substituents α to phosphorus. Organomet 23(11):2625–2632
Lecocq V, Olivier-Bourbigou H (2007) Biphasic Ni-catalyzed ethylene oligomerization in ionic liquids. Oil Gas Sci Technol 62(6):761–773
Ortiz de la Tabla L, Matas I, Palma P, Álvarez E, Cámpora J (2012) Nickel and palladium complexes with new phosphinito-imine ligands and their application as ethylene oligomerization catalysts. Organomet 31(3):1006–1016
Huang Y, Zhang L, Wei W, Alam F, Jiang T (2018) Nickel-based ethylene oligomerization catalysts supported by PNSiP ligands. Phosphorus, Sulfur Silicon Relat Elem 193(6):363–368
Peterson JD (1967) Phosphinomethyllithium compounds IV: an improved method of preparation and some synthetic applications. J Organomet Chem 8(2):199–208
Zhang L, Meng X, Chen Y, Cao C, Jiang T (2017) Chromium-based ethylene tetramerization catalysts supported by silicon-bridged diphosphine ligands: further combination of high activity and selectivity. ChemCatChem 9(1):76–79
Zhang L, Wei W, Alam F, Chen Y, Jiang T (2017) Efficient chromium-based catalysts for ethylene tri-/tetramerization switched by silicon-bridged/N,P-based ancillary ligands: a structural, catalytic and DFT study. Catal Sci Technol 7(21):5011–5018
Sheldrick GM (1996) SADABS: program for empirical absorption correction of area detector data. University of Göttingen, Göttingen
Sheldrick G (2008) A short history of SHELX. Acta Crystallogr Sect A 64(1):112–122
Dyer PW, Fawcett J, Hanton MJ (2008) Rigid N-phosphino guanidine P,N ligands and their use in nickel-catalyzed ethylene oligomerization. Organomet 27(19):5082–5087
Meng X, Zhang L, Chen Y, Jiang T (2016) Silane-bridged diphosphine ligands for nickel-catalyzed ethylene oligomerization. React Kinet Mech Catal 119(2):481–490
Sun Y, Chen Y, Mao G, Ning Y, Jiang T (2014) Boron- and silicon-bridged bis(diphenylphosphino)-type ligands for chromium-catalyzed ethylene oligomerization. Chin Sci Bull 59(21):2613–2617
Yang Q-Z, Kermagoret A, Agostinho M, Siri O, Braunstein P (2006) Nickel complexes with functional zwitterionic N,O-benzoquinonemonoimine-type ligands: syntheses, structures, and catalytic oligomerization of ethylene. Organomet 25(23):5518–5527
de Oliveira LL, Campedelli RR, Kuhn MCA, Carpentier J-F, Casagrande OL (2008) Highly selective nickel catalysts for ethylene oligomerization based on tridentate pyrazolyl ligands. J Mol Catal A: Chem 288(1):58–62
Zhang N, Wang J, Huo H, Chen L, Shi W, Li C, Wang J (2018) Iron, cobalt and nickel complexes bearing hyperbranched iminopyridyl ligands: synthesis, characterization and evaluation as ethylene oligomerization catalysts. Inorg Chim Acta 469:209–216
Aid A, Andrei RD, Amokrane S, Cammarano C, Nibou D, Hulea V (2017) Ni-exchanged cationic clays as novel heterogeneous catalysts for selective ethylene oligomerization. Appl Clay Sci 146:432–438
de Oliveira LL, da Silva SM, Casagrande ACA, Stieler R, Casagrande OL Jr (2018) Synthesis and characterization of Ni(II) complexes supported by phenoxy/naphthoxy-imine ligands with pendant N- and O-donor groups and their use in ethylene oligomerization. Appl Organomet Chem 32(7):e4414
Suo H, Zhang Y, Ma Z, Yang W, Flisak Z, Hao X, Hu X, Sun W-H (2017) 2-Chloro/phenyl-7-arylimino-6,6-dimethylcyclopenta[b]pyridylnickel chlorides: synthesis, characterization and ethylene oligomerization. Catal Commun 102:26–30
This study was supported by the National Key Research and Development Program of China (2017YFB0306700). The Natural Science Foundation of Tianjin City (14JCYBJC23100, 15JCYBJC48100 and 16JCZDJC31600).
Electronic supplementary material
About this article
Cite this article
Wei, W., Yu, B., Alam, F. et al. Ethylene oligomerization promoted by nickel-based catalysts with silicon-bridged diphosphine amine ligands. Transit Met Chem 44, 125–133 (2019). https://doi.org/10.1007/s11243-018-0276-7