Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056, Basel, Switzerland.
Chemistry. 2021 Dec 15;27(70):17688-17694. doi: 10.1002/chem.202103467. Epub 2021 Nov 11.
A ligand-controlled site-selective C(sp )-H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- to β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C-H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion.
已开发出一种使用 Pd 催化的配体控制的、杂芳基酮的 C(sp )-H 芳基化反应的位点选择性方法。该反应选择性地发生在酮侧链的α-或β-位。通过添加吡啶酮配体，可以实现从α-芳基化到β-芳基化的转换。α-芳基化过程表现出广泛的范围、高的位点和化学选择性，而β-芳基化则更为有限。机理研究表明，α-芳基化通过 C-H 活化/氧化加成/还原消除进行，而β-芳基化涉及去饱和和芳基插入。
