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Literature DB >> 24256439

Ortho vs ipso: site-selective Pd and norbornene-catalyzed arene C-H amination using aryl halides.

Abstract

A Pd and norbornene-catalyzed ortho-arene amination via Catellani-type C-H functionalization is reported. Aryl halides are used as substrates; N-benzoyloxyamines and isopropanol are employed as the amine source (oxidant) and reductant respectively. Examples are provided in 50-99% yields with high functional group tolerance. This method gives complementary site selectivity at the ortho- instead of ipso-position of aryl halides.

Entities: Chemical

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Year: 2013 PMID： 24256439 DOI： 10.1021/ja410823e

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

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Cited

27 in total

1. Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene.

Authors: Peng-Xiang Shen; Xiao-Chen Wang; Peng Wang; Ru-Yi Zhu; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-09-03 Impact factor: 15.419

2. Non-directed aromatic C-H amination: catalytic and mechanistic studies enabled by Pd catalyst and reagent design.

Authors: H M D Bandara; D Jin; M A Mantell; K D Field; A Wang; R P Narayanan; N A Deskins; M H Emmert
Journal: Catal Sci Technol Date: 2016-03-24 Impact factor: 6.119

3. Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis.

Authors: Renhe Li; Feipeng Liu; Guangbin Dong
Journal: Chem Date: 2019-03-07 Impact factor: 22.804

4. 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

5. Palladium/Norbornene Cooperative Catalysis.

Authors: Jianchun Wang; Guangbin Dong
Journal: Chem Rev Date: 2019-04-25 Impact factor: 60.622

6. Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.

Authors: Feipeng Liu; Zhe Dong; Jianchun Wang; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2019-01-16 Impact factor: 15.336

Ortho vs ipso: site-selective Pd and norbornene-catalyzed arene C-H amination using aryl halides.

1. Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene.

2. Non-directed aromatic C-H amination: catalytic and mechanistic studies enabled by Pd catalyst and reagent design.

3. Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis.

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

5. Palladium/Norbornene Cooperative Catalysis.

6. Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.

7. Compatibility Score for Rational Electrophile Selection in Pd/NBE Cooperative Catalysis.

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

9. Ligand-enabled meta-C-H activation using a transient mediator.

10. A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp(2) C-H Bond Amination.