Doyle Michael G J, Lundgren Rylan J
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Chem Commun (Camb). 2021 Mar 16;57(22):2724-2731. doi: 10.1039/d1cc00213a.
The Cu-catalyzed oxidative cross-coupling of N- and O-nucleophiles with aryl boronic acids (the Chan-Lam reaction) remains among the most useful approaches to prepare aniline and phenol derivatives. The combination of high chemoselectivity, mild reaction conditions, and the ability to use simple Cu-salts as catalysts makes this process a valuable alternative to aromatic substitutions and Pd-catalyzed reactions of aryl electrophiles (Buchwald-Hartwig coupling). Despite the widespread use of Chan-Lam reactions in synthesis, the analogous carbon-carbon bond forming variant of this process had not been developed prior to our work. This feature article describes our discovery and application of Cu-catalyzed oxidative coupling reactions of activated methylene derivatives or carboxylic acids with nucleophiles including aryl boronic esters and amines.
铜催化的N-和O-亲核试剂与芳基硼酸的氧化交叉偶联反应（Chan-Lam反应）仍然是制备苯胺和苯酚衍生物最有用的方法之一。高化学选择性、温和的反应条件以及使用简单铜盐作为催化剂的能力，使得该过程成为芳香取代反应和钯催化的芳基亲电试剂反应（Buchwald-Hartwig偶联反应）的有价值替代方法。尽管Chan-Lam反应在合成中得到广泛应用，但在我们的工作之前，该过程类似的碳-碳键形成变体尚未得到开发。这篇专题文章描述了我们对活化亚甲基衍生物或羧酸与包括芳基硼酸酯和胺在内的亲核试剂的铜催化氧化偶联反应的发现及应用。
