Palladium-Catalyzed Amination of Aromatic C−H Bonds with Oxime Esters

作者：Yichen Tan, John F. Hartwig · 发表于：Journal of the American Chemical Society · 年份：2010 · DOI：10.1021/ja100676r · 被引用次数：554 · 研究领域：Catalytic C–H Functionalization Methods、Synthesis and Catalytic Reactions、Cyclopropane Reaction Mechanisms

We report a conceptually new approach to the direct amination of aromatic C-H bonds. In this process, an oxime ester function reacts with an aromatic C-H bond under redox-neutral conditions to form, in the case studied, an indole product. These reactions occur with relatively low catalyst loading (1 mol %) by a mechanism that appears to involve an unusual initial oxidative addition of an N-O bond to a Pd(0) species. The Pd(II) complex from oxidative addition of the N-X bond has been isolated for the first time, and evidence for the intermediacy of such oxidative addition products in the catalytic reaction has been gained.