[2, 2’-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C-H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine,Journal of the American Chemical Society

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[2, 2’-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C-H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-12-06 , DOI: 10.1021/jacs.8b10680
Vanesa Salamanca ₁ , Alberto Toledo ₁ , Ana C. Albéniz ₁

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The ligand [2,2'-bipyridin]-6(1 H)-one (bipy-6-OH) has a strong accelerating effect on the Pd-catalyzed direct arylation of pyridine or arenes. The isolation of relevant intermediates and the study of their decomposition unequivocally show that the deprotonated coordinated ligand acts as a base and assists the cleavage of the C-H bond. Mechanistic work indicates that the direct arylation of pyridine with this ligand occurs through a Pd(0)/Pd(II) cycle. Because of this dual ligand-intramolecular base role, there is no need for an available coordination site on the metal for an external base, a difficulty encountered when chelating ligands are used in coupling reactions that involve a C-H cleavage step.

中文翻译：

[2, 2'-Bipyridin]-6(1H)-one，钯介导的 CH 活化步骤中真正的合作配体：吡啶直接 C-3 芳基化的实验证据

配体 [2,2'-联吡啶]-6(1 H)-one (bipy-6-OH) 对 Pd 催化的吡啶或芳烃直接芳基化具有很强的加速作用。相关中间体的分离及其分解研究明确表明，去质子化的配位配体充当碱基并有助于 CH 键的断裂。机理研究表明，吡啶与该配体的直接芳基化通过 Pd(0)/Pd(II) 循环发生。由于这种双配体-分子内碱作用，金属上不需要外部碱的可用配位位点，这是在涉及 CH 裂解步骤的偶联反应中使用螯合配体时遇到的困难。

更新日期：2018-12-06

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