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Abstract <p> The possibility of a one-step synthesis of a norbornene derivative with two organosilicon substituents via the bis-silylation reaction of norbornadiene-2,5 (NBD) with 1,1,1,2,2,2-hexamethyldisilane was investigated. As a result, 5,6-bis(trimethylsilyl)norbornene-2 (BTSNTC) was obtained with high yield and high selectivity in the presence of a palladium catalyst and an isocyanide ligand. A significant influence of the solvent nature and the introduction of basic additives on the reaction rate and the maximum achievable NBD conversions was demonstrated. The optimal solvents and additives are toluene, 1,4-dioxane, and potassium <i>tert</i>-butoxide, respectively.</p>

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One-Step Synthesis of a Silicon-substituted Norbornene Derivative Using the Bis-Silylation Reaction of Norbornadiene-2,5 with 1,1,1,2,2,2-Hexamethyldisilane

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • P. P. Lezhnin,
  • M. V. Bermeshev

摘要

Abstract

The possibility of a one-step synthesis of a norbornene derivative with two organosilicon substituents via the bis-silylation reaction of norbornadiene-2,5 (NBD) with 1,1,1,2,2,2-hexamethyldisilane was investigated. As a result, 5,6-bis(trimethylsilyl)norbornene-2 (BTSNTC) was obtained with high yield and high selectivity in the presence of a palladium catalyst and an isocyanide ligand. A significant influence of the solvent nature and the introduction of basic additives on the reaction rate and the maximum achievable NBD conversions was demonstrated. The optimal solvents and additives are toluene, 1,4-dioxane, and potassium tert-butoxide, respectively.