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Literature DB >> 28066540

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

H M D Bandara¹, D Jin¹, M A Mantell¹, K D Field¹, A Wang¹, R P Narayanan¹, N A Deskins², M H Emmert¹.

Abstract

This manuscript describes the systematic development of pyridine-type ligands, which promote the Pd catalyzed, non-directed amination of benzene in combination with novel, hydroxylamine-based electrophilic amination reagents. DFT calculations and mechanistic experiments provide insights into the factors influencing the arene C-H amination protocol.

Entities: Chemical Disease Species

Year: 2016 PMID： 28066540 PMCID： PMC5215025 DOI： 10.1039/C6CY00457A

Source DB: PubMed Journal: Catal Sci Technol ISSN： 2044-4753 Impact factor: 6.119

29 in total

1. Pyridine ligands as promoters in Pd(II/0)-catalyzed C-H olefination reactions.

Authors: Asako Kubota; Marion H Emmert; Melanie S Sanford
Journal: Org Lett Date: 2012-03-12 Impact factor: 6.005

2. Remarkably high reactivity of Pd(OAc)2/pyridine catalysts: nondirected C-H oxygenation of arenes.

Authors: Marion H Emmert; Amanda K Cook; Yushu J Xie; Melanie S Sanford
Journal: Angew Chem Int Ed Engl Date: 2011-08-24 Impact factor: 15.336

3. Platinum and palladium complexes containing cationic ligands as catalysts for arene H/D exchange and oxidation.

Authors: Marion H Emmert; J Brannon Gary; Janette M Villalobos; Melanie S Sanford
Journal: Angew Chem Int Ed Engl Date: 2010-08-09 Impact factor: 15.336

4. Beyond directing groups: transition-metal-catalyzed C-H activation of simple arenes.

Authors: Nadine Kuhl; Matthew N Hopkinson; Joanna Wencel-Delord; Frank Glorius
Journal: Angew Chem Int Ed Engl Date: 2012-09-20 Impact factor: 15.336

5. Transition-metal-catalyzed C-N bond forming reactions using organic azides as the nitrogen source: a journey for the mild and versatile C-H amination.

Authors: Kwangmin Shin; Hyunwoo Kim; Sukbok Chang
Journal: Acc Chem Res Date: 2015-03-30 Impact factor: 22.384

6. Aerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed C-H Functionalization.

Authors: Yusuke Izawa; Shannon S Stahl
Journal: Adv Synth Catal Date: 2010-12-17 Impact factor: 5.837

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

1. Pyridine ligands as promoters in Pd(II/0)-catalyzed C-H olefination reactions.

2. Remarkably high reactivity of Pd(OAc)2/pyridine catalysts: nondirected C-H oxygenation of arenes.

3. Platinum and palladium complexes containing cationic ligands as catalysts for arene H/D exchange and oxidation.

4. Beyond directing groups: transition-metal-catalyzed C-H activation of simple arenes.

5. Transition-metal-catalyzed C-N bond forming reactions using organic azides as the nitrogen source: a journey for the mild and versatile C-H amination.

6. Aerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed C-H Functionalization.

7. C-H nitrogenation and oxygenation by ruthenium catalysis.

8. Sterically controlled, palladium-catalyzed intermolecular amination of arenes.

9. The catalytic cross-coupling of unactivated arenes.

10. Copper-catalyzed C(sp2)-H amidation of unactivated arenes by N-tosyloxycarbamates.

1. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

2. Cu(II) carboxylate arene C─H functionalization: Tuning for nonradical pathways.