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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

preprint
submitted on 10.12.2020, 11:54 and posted on 11.12.2020, 07:55 by Sergey Zubkevich, Vladislav Tuskaev, Svetlana Gagieva, Alexander Pavlov, Viktor N. Khrustalev, Anton Kosov, Olga Polyakova, Dmitry N. Zarubin, Elena G. Kononova, Valeria N. Talanova, Boris M. Bulychev
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, MALDI-TOF 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).

Funding

Russian Foundation for Basic Research, Project № 18-03-01112

Council of the President of the Russian Federation, Project МК-199.2019.3

RUDN University Strategic Academic Leadership Program

Government of the Russian Federation budget support (reg. №АААА-А16-116053110012-5)

History

Email Address of Submitting Author

zubkevich.sergey@gmail.com

Institution

Lomonosov Moscow State University

Country

Russian Federation

ORCID For Submitting Author

0000-0001-5371-0901

Declaration of Conflict of Interest

The authors declare no conflicts of interest.

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