Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel.
J Org Chem. 2021 Jan 1;86(1):79-90. doi: 10.1021/acs.joc.0c00874. Epub 2020 Dec 9.
The selective FeCl-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing ,-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.
研究了选择性 FeCl3 催化的酚类和伯、仲、叔 2-氨基萘衍生物之间的氧化交叉偶联反应。这种可扩展方法的通用性为制备广泛用作配体和催化剂的 -联芳基化合物提供了一种可持续的替代方法。基于全面的动力学研究，提出了一个涉及三元配合物的催化循环，该配合物在关键的氧化偶联步骤中同时结合偶联物和氧化剂。此外，研究表明该反应受非循环酸碱和配体交换过程的调控。
