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<p>The oxidative coupling of internal alkynes with arylboronic acids catalyzed by palladium compounds is a convenient tool for the preparation of polyaryl-substituted unsaturated compounds. For this type of reactions, the question about the nature of the catalytically active species remains unanswered to date and cannot be answered using the data about true catalyst nature in the related reaction because of the difficulties in the determination of active catalyst for the reactions. The problem cannot be solved using the results available for the related systems. The coincidence of the differential selectivities to tetraphenylethylene and tetraphenylnapthalene formed in the oxidative coupling of diphenylacetylene with phenylboronic acid when using a number of individual palladium compounds and insoluble solid-phase palladium-containing compositions (such as Pd<sup>II</sup>/Al<sub>2</sub>O<sub>3</sub>, Pd<sup>0</sup>/C, <i>etc.</i>) indicates that the reaction proceeds in the solution <i>via</i> the homogeneous catalysis mechanism involving molecular complexes and low-nuclearity clusters of palladium existing in the liquid phase.</p>

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Homogeneous and heterogeneous mechanisms of catalysis in the oxidative coupling of diphenylacetylene with phenylboronic acid in the presence of palladium

  • 期刊论文

  • 发表日期：

    2025年3月1日

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  • E. V. Larina,
  • N. A. Lagoda,
  • A. A. Kurokhtina,
  • A. F. Schmidt

摘要

The oxidative coupling of internal alkynes with arylboronic acids catalyzed by palladium compounds is a convenient tool for the preparation of polyaryl-substituted unsaturated compounds. For this type of reactions, the question about the nature of the catalytically active species remains unanswered to date and cannot be answered using the data about true catalyst nature in the related reaction because of the difficulties in the determination of active catalyst for the reactions. The problem cannot be solved using the results available for the related systems. The coincidence of the differential selectivities to tetraphenylethylene and tetraphenylnapthalene formed in the oxidative coupling of diphenylacetylene with phenylboronic acid when using a number of individual palladium compounds and insoluble solid-phase palladium-containing compositions (such as PdII/Al2O3, Pd0/C, etc.) indicates that the reaction proceeds in the solution via the homogeneous catalysis mechanism involving molecular complexes and low-nuclearity clusters of palladium existing in the liquid phase.