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

Atsushi Kaga; Hirohito Hayashi; Hiroyuki Hakamata; Miku Oi; Masanobu Uchiyama; Ryo Takita; Shunsuke Chiba

doi:10.1002/anie.201705916

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

Atsushi Kaga, Hirohito Hayashi, Hiroyuki Hakamata, Miku Oi, Masanobu Uchiyama, Ryo Takita^*, Shunsuke Chiba

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

79 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	11807-11811
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	39
DOIs	https://doi.org/10.1002/anie.201705916
Publication status	Published - Sept 18 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

amination
DFT calculations
nitrogen heterocycles
nucleophilic aromatic substitution
sodium hydride

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10.1002/anie.201705916

Cite this

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AU - Kaga, Atsushi

AU - Hayashi, Hirohito

AU - Hakamata, Hiroyuki

AU - Oi, Miku

AU - Uchiyama, Masanobu

AU - Takita, Ryo

AU - Chiba, Shunsuke

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AB - 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.

KW - amination

KW - DFT calculations

KW - nitrogen heterocycles

KW - nucleophilic aromatic substitution

KW - sodium hydride

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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