Literature DB >> 15624951

Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents.

Ashley M Berman1, Jeffrey S Johnson.   

Abstract

The copper-catalyzed electrophilic amination of functionalized diarylzinc reagents with O-acyl hydroxylamines allows for the preparation of functionalized tertiary arylamines in high yields, and is noteworthy for the mild reaction conditions employed. The functionalized diarylzinc reagents were prepared via an iodine/magnesium exchange of the corresponding aryl iodide followed by transmetalation of the resultant Grignard species with ZnCl(2).

Entities:  

Year:  2005        PMID: 15624951     DOI: 10.1021/jo048168g

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


  12 in total

1.  A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-12       Impact factor: 15.336

2.  Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors:  Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

Review 3.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

4.  Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

Authors:  Tanner W Bingham; Lucas W Hernandez; Daniel G Olson; Riley L Svec; Paul J Hergenrother; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

5.  An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.

Authors:  Zhishi Ye; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

6.  Copper-Catalyzed Electrophilic Amination of Heteroaromatic and Aromatic C-H Bonds via TMPZnCl•LiCl Mediated Metalation.

Authors:  Stacey L McDonald; Charles E Hendrick; Katie J Bitting; Qiu Wang
Journal:  Organic Synth       Date:  2015-11-17

7.  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

8.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

9.  Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.

Authors:  Stacey L McDonald; Charles E Hendrick; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-25       Impact factor: 15.336

10.  Directed regioselective ortho,ortho'-magnesiations of aromatics and heterocycles using sBu2Mg in toluene.

Authors:  Andreas Hess; Jan P Prohaska; Sabrina B Doerrich; Florian Trauner; Ferdinand H Lutter; Sébastien Lemaire; Simon Wagschal; Konstantin Karaghiosoff; Paul Knochel
Journal:  Chem Sci       Date:  2021-05-18       Impact factor: 9.825

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