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

Authors

  • Viacheslav P. 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

Keywords:

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

Abstract

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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Published

2026-02-24

Issue

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

Section

Short Communications