High Turnover Number and Rapid, Room-Temperature Amination of Chloroarenes Using Saturated Carbene Ligands

作者：Shaun R. Stauffer, Sunwoo Lee, James P. Stambuli, Sheila I. Hauck, John F. Hartwig · 发表于：Organic Letters · 年份：2000 · DOI：10.1021/ol005751k · 被引用次数：317 · 研究领域：Catalytic Cross-Coupling Reactions、N-Heterocyclic Carbenes in Organic and Inorganic Chemistry、Catalytic C–H Functionalization Methods

A catalytic system for the mild amination of aryl chlorides is described. This system consists of a Pd(0) precursor and a dihydroimidazoline carbene ligand, which is generated in situ from its protonated tetrafluoroborate salt ( 2 ). Using this catalyst, aryl and heteroaryl chlorides react with secondary amines and anilines within hours at room temperature. Turnover numbers as high as 5000 are obtained at elevated temperatures for reaction of morpholine with an unactivated aryl chloride.