Literature DB >> 28741890

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

Atsushi Kaga1, Hirohito Hayashi1, Hiroyuki Hakamata1, Miku Oi2,3, Masanobu Uchiyama2,3, Ryo Takita2, Shunsuke Chiba1.   

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

Entities:  

Keywords:  DFT calculations; amination; nitrogen heterocycles; nucleophilic aromatic substitution; sodium hydride

Year:  2017        PMID： 28741890     DOI： 10.1002/anie.201705916

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  Concerted Nucleophilic Aromatic Substitution Reactions.

Authors:  Simon Rohrbach; Andrew J Smith; Jia Hao Pang; Darren L Poole; Tell Tuttle; Shunsuke Chiba; John A Murphy
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-13       Impact factor: 15.336

2.  Aggregation and Solvation of Sodium Hexamethyldisilazide: Across the Solvent Spectrum.

Authors:  Ryan A Woltornist; David B Collum
Journal:  J Org Chem       Date:  2021-01-20       Impact factor: 4.354

3.  Cation Radical-Accelerated Nucleophilic Aromatic Substitution for Amination of Alkoxyarenes.

Authors:  Nicholas J Venditto; David A Nicewicz
Journal:  Org Lett       Date:  2020-06-02       Impact factor: 6.005

4.  LiCl-promoted amination of β-methoxy amides (γ-lactones).

Authors:  Ru Zhao; Bing-Lin Zeng; Wen-Qiang Jia; Hong-Yi Zhao; Long-Ying Shen; Xiao-Jian Wang; Xian-Dao Pan
Journal:  RSC Adv       Date:  2020-09-21       Impact factor: 4.036

5.  Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

Authors:  Tamie Suzuki; Nilamber A Mate; Arijit A Adhikari; John D Chisholm
Journal:  Molecules       Date:  2019-11-15       Impact factor: 4.411

6.  Et3SiH + KO t Bu provide multiple reactive intermediates that compete in the reactions and rearrangements of benzylnitriles and indolenines.

Authors:  Andrew J Smith; Daniela Dimitrova; Jude N Arokianathar; Kenneth F Clark; Darren L Poole; Stuart G Leach; John A Murphy
Journal:  Chem Sci       Date:  2020-10-21       Impact factor: 9.825
  6 in total

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