Copper-Catalyzed ortho -Selective Dearomative C–N Coupling of Simple Phenols with O -Benzoylhydroxylamines

作者：Zhili Yao, Lei Wang, Nanqi Shao, Yinlong Guo, Dong‐Hui Wang · 发表于：ACS Catalysis · 年份：2019 · DOI：10.1021/acscatal.9b01317 · 被引用次数：26 · 研究领域：Catalytic C–H Functionalization Methods、Radical Photochemical Reactions、Oxidative Organic Chemistry Reactions

A Cu-catalyzed dearomative amination of simple phenols with O -benzoylhydroxylamines (R′RN–OBz) to synthesize α-aminocyclohexa-2,4-dienones is reported. This intermolecular transformation occurs exclusively at the position ortho to the hydroxyl group, providing a convenient method to synthesize the desired products in high yields. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. Mechanistic studies indicate that this transformation proceeds via either (1) a single-electron transfer process involving attack of an N -centered radical onto the phenol or (2) a two-electron pathway involving addition of phenol to an electrophilic Cu III –amino complex via an inner-sphere process.