SYNTHESIS OF ARYLPYRIDINES BY Pd(II) COORDINATION POLYMER CATALYZED C–C COUPLING

Авторы

  • Viacheslav Pashkevysh L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028. Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Vasiliy I. Vasiliy I. Yenya Enamine Ltd., 78 Winston Churchill St., Kyiv 02094. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kuharya St., Kyiv 02094
  • Ivan O. Kryvosheia Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Igor Ye. Kotenko L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028.
  • Daryna V. Kustenko L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028. Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Konstantin S. Gavrilenko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094. Department of Chemistry, Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01033
  • Sergey V. Kolotilov L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028. Enamine Ltd., 78 Winston Churchill St., Kyiv 02094

Ключевые слова:

boronic acids, palladium, phenyl pyridine, C–C coupling, coordination polymer, nanoparticles

Аннотация

The study was aimed on elucidation of the applicability of Pd(II) coordination polymer [Pd(2-Pymo)2]n (where 2-Pymo– is 2-hydroxypyrimidine anion) as catalyst for C–C coupling of heterocyclic compounds. It was shown that [Pd(2-Pymo)2]n catalyzes C–C coupling of isomeric bromopyridines and arylboronic acids with up to 70% yield at 1 mol % Pd loading, affording the respective phenylpyridines. Coupling of 3-pyridineboronic acid and bromobenzene in presence of [Pd(2-Pymo)2]n gave 3-phenylpyridine with 75% yield at 3 mol % Pd loading. At the same time, the method was not suitable for C–C coupling reactions, involving pyrazoles (both bromopyrazole and pyrazoleboronic acids) and 2-bromopyrimidine. The reaction of phenylboronic acid and 3-bromopyridine proceeded with an induction period, presumably required for in situ formation of ultrafine Pd nanoparticles, responsible for the catalytic activity of [Pd(2-Pymo)2]n. The advantage of the catalyst is low consumption of Pd, which is washed out from the surface of the coordination polymer particles, as well as low price of [Pd(2-Pymo)2]n compared to Pd complexes with phosphines. The solid catalyst may be easily separated after the reaction and reused or regenerated.

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Опубликован

2026-02-24

Выпуск

Том 61 № 9/10 (2025): Modern catalytic approaches for the assembly and functionalization of heterocyclic compounds

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