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Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite
Author(s) -
Kaga Atsushi,
Hayashi Hirohito,
Hakamata Hiroyuki,
Oi Miku,
Uchiyama Masanobu,
Takita Ryo,
Chiba Shunsuke
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705916
Subject(s) - amination , chemistry , iodide , nucleophile , sodium hydride , nucleophilic substitution , hydride , sodium iodide , nucleophilic aromatic substitution , organic chemistry , ethyl iodide , medicinal chemistry , sodium , lithium (medication) , iodine , catalysis , medicine , endocrinology , hydrogen
A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.