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RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Copper Nanoparticles and Copper-Containing Metal-Organic Coordination Polymers in the Catalytic Amination of 2-Halopyridines

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PII
S30346304S0514749225040011-1
DOI
10.7868/S3034630425040011
Publication type
Article
Status
Published
Authors
D.A. Leksakov
  • Affiliation:
    Department of Chemistry, Lomonosov Moscow State University
    A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS
A.S. Borisova
  • Affiliation: Department of Chemistry, Lomonosov Moscow State University
A.V. Murashkina
  • Affiliation: Department of Chemistry, Lomonosov Moscow State University
D.S. Kuliukhina
  • Affiliation: Department of Chemistry, Lomonosov Moscow State University
A.D. Averin
  • Affiliation:
    Department of Chemistry, Lomonosov Moscow State University
    A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS
V.V. Vergun
  • Affiliation: N.D. Zelinsky Institute of Organic Chemistry RAS
V.I. Isaeva
  • Affiliation: N.D. Zelinsky Institute of Organic Chemistry RAS
E.N. Savelyev
  • Affiliation: Volgograd State Technical University
I.A. Novakov
  • Affiliation: Volgograd State Technical University
I.P. Beletskaya
  • Affiliation:
    Department of Chemistry, Lomonosov Moscow State University
    A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS
Volume/ Edition
Volume 61 / Issue number 4
Pages
353-363
Abstract
The efficiency of copper-containing metal-organic coordination polymers (Cu-MOFs) and commercially available non-immobilized copper nanoparticles (CuNPs) in the amination of 2-iodopyridine, 2-bromopyridine and its trifluoromethyl derivatives with -octylamine and adamantane-containing amines with different steric hindrances at the amino group was compared. The yields of the amination products under optimized conditions were shown to be close for both catalytic systems. To achieve good yields in the case of 2-bromopyridine, an increase in the concentration of reagents and the use of 2 equiv. of haloarene are required, while the introduction of a trifluoromethyl group at position 6 of the pyridine ring improves the yields of the amination products. Increasing steric hindrances at the amino group leads to a noticeable decrease in the yields of products in the Cu-MOF catalyzed reactions. However, the use of CuNPs allows for successful reactions with such amines, and CuNPs of 25 nm average size demonstrated an advantage over bifractional nanoparticles of 10/80 nm. On the other hand, increasing the concentration of reagents in the Cu-MOF catalyzed reactions provides good yields of the target compounds without addition ligands.
Keywords
аминирование пиридин галогенарены амины адамантан наночастицы меди металлорганические координационные полимеры
Date of publication
13.12.2025
Year of publication
2025
Number of purchasers
0
Views
23

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