Literature DB >> 21261263

A facile and practical copper powder-catalyzed, organic solvent- and ligand-free Ullmann amination of aryl halides.

Jiao Jiao1, Xi-Ru Zhang, Ning-Hui Chang, Jie Wang, Jun-Fa Wei, Xian-Ying Shi, Zhan-Guo Chen.   

Abstract

A facile and practical method that the copper powder-catalyzed Ullmann amination of aryl halides with aqueous methylamine under organic solvent- and ligand-free condition at 100 °C and in air gave N-arylamines as sole products in good to excellent yields. The presence of a small amount of air is essential. Other aliphatic primary amines show good to very high reactivity. Secondary amines and aniline are not reactive. Sensitive substituents (i.e., CHO, MeCO, CN and Cl) are tolerable in the reaction.
© 2011 American Chemical Society

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Year:  2011        PMID： 21261263     DOI： 10.1021/jo102169t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  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

2.  Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor.

Authors:  Cheng Zhang; C James Chou
Journal:  Org Lett       Date:  2016-10-19       Impact factor: 6.005

3.  RECENT SYNTHETIC DEVELOPMENTS AND APPLICATIONS OF THE ULLMANN REACTION. A REVIEW.

Authors:  Hao Lin; Dianqing Sun
Journal:  Org Prep Proced Int       Date:  2013       Impact factor: 1.628

4.  Synthesis, characterisation and reactivity of copper(I) amide complexes and studies on their role in the modified Ullmann amination reaction.

Authors:  Simon Sung; D Christopher Braddock; Alan Armstrong; Colin Brennan; David Sale; Andrew J P White; Robert P Davies
Journal:  Chemistry       Date:  2015-03-18       Impact factor: 5.236

5.  N-aryl lactams by regioselective ozonation of N-aryl cyclic amines.

Authors:  Francesco Saliu; Marco Orlandi; Maurizio Bruschi
Journal:  ISRN Org Chem       Date:  2012-09-18

6.  Cu(0) nanoparticles deposited on nanoporous polymers: a recyclable heterogeneous nanocatalyst for Ullmann coupling of aryl halides with amines in water.

Authors:  John Mondal; Anup Biswas; Shunsuke Chiba; Yanli Zhao
Journal:  Sci Rep       Date:  2015-02-06       Impact factor: 4.379

7.  Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C-N Coupling Reactions With No Additional Ligands.

Authors:  Andrea Francesca Quivelli; Paola Vitale; Filippo Maria Perna; Vito Capriati
Journal:  Front Chem       Date:  2019-10-30       Impact factor: 5.221

8.  Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos).

Authors:  Ilja Rodstein; Daniel Sowa Prendes; Leon Wickert; Maurice Paaßen; Viktoria H Gessner
Journal:  J Org Chem       Date:  2020-09-21       Impact factor: 4.354

9.  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
  9 in total

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