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Literature DB >> 28857476

Buchwald-Hartwig Amination of Nitroarenes.

Fumiyoshi Inoue¹, Myuto Kashihara¹, M Ramu Yadav¹, Yoshiaki Nakao¹.

Abstract

The Buchwald-Hartwig amination of nitroarenes was achieved for the first time by using palladium catalysts bearing dialkyl(biaryl)phosphine ligands. These cross-coupling reactions of nitroarenes with diarylamines, arylamines, and alkylamines afforded the corresponding substituted arylamines. A catalytic cycle involving the oxidative addition of the Ar-NO2 bond to palladium(0) followed by nitrite/amine exchange is proposed based on a stoichiometric reaction.

Entities: Chemical

Keywords: C−N activation; amination; cross-coupling; nitroarenes; palladium

Year: 2017 PMID： 28857476 DOI： 10.1002/anie.201706982

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

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Cited

11 in total

1. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors: Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal: ACS Catal Date: 2020-09-10 Impact factor: 13.084

2. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors: Louis-Charles Campeau; Nilay Hazari
Journal: Organometallics Date: 2018-11-27 Impact factor: 3.876

Review 3. Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones.

Authors: Feiyue Hao; Nagatoshi Nishiwaki
Journal: Molecules Date: 2020-02-05 Impact factor: 4.411

4. 2-Fluoro-5-nitrophenyldiazonium: A Novel Sanger-Type Reagent for the Versatile Functionalization of Alcohols.

Authors: Oliver Fischer; Markus R Heinrich
Journal: Chemistry Date: 2021-02-24 Impact factor: 5.236

5. Suzuki-Miyaura Cross-Coupling of Esters by Selective O-C(O) Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]₂ Precatalysts: Catalyst Evaluation and Mechanism.

Authors: Shiyi Yang; Tongliang Zhou; Albert Poater; Luigi Cavallo; Steven P Nolan; Michal Szostak
Journal: Catal Sci Technol Date: 2021-03-25 Impact factor: 6.119

6. A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent.

Authors: Boya Feng; Yudong Yang; Jingsong You
Journal: Chem Sci Date: 2020-05-25 Impact factor: 9.825

Buchwald-Hartwig Amination of Nitroarenes.

1. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

2. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Review 3. Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones.

4. 2-Fluoro-5-nitrophenyldiazonium: A Novel Sanger-Type Reagent for the Versatile Functionalization of Alcohols.

5. Suzuki-Miyaura Cross-Coupling of Esters by Selective O-C(O) Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]₂ Precatalysts: Catalyst Evaluation and Mechanism.

6. A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent.

7. Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols.

8. Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: complex lactams via carboamination.

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

10. Sustainable ppm level palladium-catalyzed aminations in nanoreactors under mild, aqueous conditions.