Literature DB >> 12167031

A new general preparation of polyfunctional diarylamines by the addition of functionalized arylmagnesium compounds to nitroarenes.

Ioannis Sapountzis1, Paul Knochel.   

Abstract

The addition of functionalized arylmagnesium halides to nitroarenes in THF (-20 degrees C, 2 h) provides, after reductive workup (FeCl(2), NaBH(4)), various polyfunctional diarylamines in 63-86% yield. Heterocyclic arylated amines can be prepared by this one-pot procedure. A mechanistic rationale of this reaction is given.

Entities:  

Year:  2002        PMID： 12167031     DOI： 10.1021/ja026718r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

1.  PEt3-Mediated Deoxygenative C-N Coupling of Nitroarenes and Boronic Acids.

Authors:  Trevor V Nykaza; Junyu Yang; Alexander T Radosevich
Journal:  Tetrahedron       Date:  2019-03-25       Impact factor: 2.457

2.  P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

Authors:  Gen Li; Ziyang Qin; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

3.  Reductive N-alkylation of nitroarenes: a green approach for the N-alkylation of natural products.

Authors:  Amir E Wahba; Mark T Hamann
Journal:  J Org Chem       Date:  2012-04-30       Impact factor: 4.354

4.  Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines.

Authors:  Xinyu Guan; Haoran Zhu; Tom G Driver
Journal:  ACS Catal       Date:  2021-09-23       Impact factor: 13.700

5.  Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates.

Authors:  Pritam Roychowdhury; Roberto G Herrera; Hao Tan; David C Powers
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-20       Impact factor: 16.823

6.  Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

Authors:  Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
Journal:  J Org Chem       Date:  2012-10-19       Impact factor: 4.354

7.  Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV═O Catalysis.

Authors:  Trevor V Nykaza; Julian C Cooper; Gen Li; Nolwenn Mahieu; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2018-11-02       Impact factor: 15.419

8.  PIII /PV =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

Authors:  Trevor V Nykaza; Gen Li; Junyu Yang; Michael R Luzung; Alexander T Radosevich
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-29       Impact factor: 15.336

9.  Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.

Authors:  Yingwei Zhao; Haoran Zhu; Siyoung Sung; Donald J Wink; Joseph M Zadrozny; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-20       Impact factor: 16.823

10.  Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid.

Authors:  Silvia Roscales; Aurelio G Csákÿ
Journal:  ACS Omega       Date:  2019-08-12
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