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Trapping the Short-Chain Odd Carbon Number Olefins Using Nickel(II)-catalyzed Tandem Ethylene Oligomerization and Friedel-Crafts Alkylation of Toluene
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  • Sergey Zubkevich,
  • Vladislav Tuskaev,
  • Svetlana Gagieva,
  • Alexander Pavlov,
  • Viktor Khrustalev,
  • Fei Wang,
  • Li Pan,
  • Yue-Sheng Li,
  • Daniele Saracheno,
  • Anton Vikhrov,
  • Dmitry Zarubin,
  • Boris Bulychev
Sergey Zubkevich
Lomonosov Moscow State University Department of Chemistry
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Vladislav Tuskaev
Lomonosov Moscow State University Department of Chemistry
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Svetlana Gagieva
Lomonosov Moscow State University Department of Chemistry
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Alexander Pavlov
FSBSI A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
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Viktor Khrustalev
Peoples' Friendship University of Russia
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Fei Wang
Tianjin University
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Li Pan
Tianjin University

Corresponding Author:[email protected]

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Yue-Sheng Li
Tianjin University
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Daniele Saracheno
FSBSI A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
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Anton Vikhrov
FSBSI A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
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Dmitry Zarubin
FSBSI A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
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Boris Bulychev
Lomonosov Moscow State University Faculty of Chemistry
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Abstract

Nickel(II) complexes with pyrazole-based ligands are widely employed in catalysis of ethylene oligomerization and subsequent Friedel-Crafts alkylation of toluene. We have prepared ten new nickel(II) dibromide complexes with various substituted bis(azolyl)methanes. They have been characterized using 1H NMR, IR, high resolution mass spectrometry and elemental analysis. The structures of three complexes have been unambiguously established using X-ray diffraction. It was found that these complexes in the presence of Et2AlCl or Et3Al2Cl3 are active both in ethylene oligomerization and Friedel-Crafts alkylation processes (activity up to 3720 kgoligomer·mol[Ni]−1·h−1). The use of Et3Al2Cl3 results in the higher share of alkylated products (up to 60%). Moreover, catalytic systems activated with Et3Al2Cl3 produced small amounts of odd carbon number olefins (up to 0.8%). The Friedel-Crafts alkylation was used as a trap for previously undetected short-chain odd carbon number olefins (C3 and C5).
28 May 20231st Revision Received
29 May 2023Submission Checks Completed
29 May 2023Assigned to Editor
29 May 2023Review(s) Completed, Editorial Evaluation Pending
29 May 2023Editorial Decision: Accept