Literature DB >> 20877862

Direct amination of aryl halides with ammonia.

Yoann Aubin1, Cédric Fischmeister, Christophe M Thomas, Jean-Luc Renaud.   

Abstract

The traditional homogeneous access to aromatic amine derivatives is a nucleophilic aromatic substitution of the corresponding aryl halides. The halogen atom is usually relatively inert to amination reaction unless it is activated by the presence of electron withdrawing groups. Consequently, there has been particular emphasis over the past decade on the synthesis of metal complexes that are active catalysts for the preparation of aromatic amines. This tutorial review focuses on the use of metal-based complexes for the direct amination of aryl halides with ammonia.

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Year:  2010        PMID: 20877862     DOI: 10.1039/c003692g

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  10 in total

1.  Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.

Authors:  Chi Wai Cheung; David S Surry; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-01       Impact factor: 6.005

Review 2.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

3.  Elusive metal-free primary amination of arylboronic acids: synthetic studies and mechanism by density functional theory.

Authors:  Chen Zhu; Gongqiang Li; Daniel H Ess; John R Falck; László Kürti
Journal:  J Am Chem Soc       Date:  2012-10-25       Impact factor: 15.419

Review 4.  The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses.

Authors:  Arun K Ghosh; Anindya Sarkar; Margherita Brindisi
Journal:  Org Biomol Chem       Date:  2018-02-26       Impact factor: 3.876

5.  Palladium-catalyzed amination of aryl chlorides and bromides with ammonium salts.

Authors:  Rebecca A Green; John F Hartwig
Journal:  Org Lett       Date:  2014-08-18       Impact factor: 6.005

6.  Versatile routes for synthesis of diarylamines through acceptorless dehydrogenative aromatization catalysis over supported gold-palladium bimetallic nanoparticles.

Authors:  Kento Taniguchi; Xiongjie Jin; Kazuya Yamaguchi; Kyoko Nozaki; Noritaka Mizuno
Journal:  Chem Sci       Date:  2016-12-01       Impact factor: 9.825

7.  On-line Ammonia Sensor and Invisible Security Ink by Fluorescent Zwitterionic Spirocyclic Meisenheimer Complex.

Authors:  Tanmay Das; Apurba Pramanik; Debasish Haldar
Journal:  Sci Rep       Date:  2017-01-16       Impact factor: 4.379

8.  Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride.

Authors:  Bao Gao; Guoying Zhang; Xibing Zhou; Hanmin Huang
Journal:  Chem Sci       Date:  2017-10-24       Impact factor: 9.825

9.  Synthesis of arylamines and N-heterocycles by direct catalytic nitrogenation using N2.

Authors:  Kai Wang; Zi-Hao Deng; Si-Jun Xie; Dan-Dan Zhai; Hua-Yi Fang; Zhang-Jie Shi
Journal:  Nat Commun       Date:  2021-01-11       Impact factor: 14.919

10.  Alkyl coupling in tertiary amines as analog of Guerbet condensation reaction.

Authors:  Yage Zhou; Dan Wu; Willinton Yesid Hernández; Changru Ma; Huangyang Su; Vitaly Ordomsky
Journal:  RSC Adv       Date:  2019-03-28       Impact factor: 3.361

  10 in total

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