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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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 39; pp. 11807 - 11811
Main Authors Kaga, Atsushi, Hayashi, Hirohito, Hakamata, Hiroyuki, Oi, Miku, Uchiyama, Masanobu, Takita, Ryo, Chiba, Shunsuke
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.09.2017
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Amination
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
DFT calculations
Iodides
Lithium
nitrogen heterocycles
nucleophilic aromatic substitution
Physical Sciences
Science & Technology
Sodium
sodium hydride
MECHANISM
AMIDE
IONS
AROMATIC-SUBSTITUTION
DFT calculations
REARRANGEMENT
sodium hydride
ETHERS
nitrogen heterocycles
amination
GENERATION
nucleophilic aromatic substitution
CYCLIZATION
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Summary: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.
Bibliography:These authors contributed equally to this work.
KAKEN
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201705916