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

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 conc...

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Veröffentlicht in:	Angewandte Chemie International Edition 2017-09, Vol.56 (39), p.11807-11811
Hauptverfasser:	Kaga, Atsushi, Hayashi, Hirohito, Hakamata, Hiroyuki, Oi, Miku, Uchiyama, Masanobu, Takita, Ryo, Chiba, Shunsuke
Format:	Artikel
Sprache:	eng
Schlagworte:	Amination Aromatic compounds DFT calculations Iodides Lithium nitrogen heterocycles nucleophilic aromatic substitution Sodium sodium hydride
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Beschreibung
Zusammenfassung:	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. Come full circle: 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.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201705916