Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite

• DOI: 10.1002/anie.201705916
• Publication Date: 2017-07-25T10:49:36Z
• Authors: Atsushi Kaga; Hirohito Hayashi; Hiroyuki Hakamata; Miku Oi; Masanobu Uchiyama; Ryo Takita; Shunsuke Chiba
• Keywords: Sodium hydride; Sodium iodide

Abstract A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in presence lithium iodide (LiI). This offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that reaction proceeds through unusual concerted aromatic substitution.