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Literature DB >> 21399704

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

Abstract

An improved method for direct oxidative coupling of o-xylene could provide streamlined access to an important monomer used in polyimide resins. The use of 2-fluoropyridine as a ligand has been found to enable unprecedented levels of chemo- and regioselectivity in this Pd-catalyzed aerobic oxidative coupling reaction. Preliminary insights have been obtained into the origin of the effectiveness of 2-fluoropyridine as a ligand.

Entities: Chemical Disease Gene

Year: 2010 PMID： 21399704 PMCID： PMC3049937 DOI： 10.1002/adsc.201000771

Source DB: PubMed Journal: Adv Synth Catal ISSN： 1615-4150 Impact factor: 5.837

21 in total

1. Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components.

Authors: Bi-Jie Li; Shi-Liang Tian; Zhao Fang; Zhang-Jie Shi
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

Authors: Gordon Brasche; Jorge García-Fortanet; Stephen L Buchwald
Journal: Org Lett Date: 2008-05-09 Impact factor: 6.005

3. Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations.

Authors: Kami L Hull; Erica L Lanni; Melanie S Sanford
Journal: J Am Chem Soc Date: 2006-11-01 Impact factor: 15.419

4. Asymmetric intermolecular heck-type reaction of acyclic alkenes via oxidative palladium(II) catalysis.

Authors: Kyung Soo Yoo; Chan Pil Park; Cheol Hwan Yoon; Satoshi Sakaguchi; Justin O'Neill; Kyung Woon Jung
Journal: Org Lett Date: 2007-08-31 Impact factor: 6.005

5. Palladium-catalyzed oxidative alkynylation of alkenes via C-C bond bleavage under oxygen atmosphere.

Authors: Takahiro Nishimura; Hitoshi Araki; Yasunari Maeda; Sakae Uemura
Journal: Org Lett Date: 2003-08-21 Impact factor: 6.005

6. Mechanistic characterization of aerobic alcohol oxidation catalyzed by Pd(OAc)(2)/pyridine including identification of the catalyst resting state and the origin of nonlinear [catalyst] dependence.

Authors: Bradley A Steinhoff; Ilia A Guzei; Shannon S Stahl
Journal: J Am Chem Soc Date: 2004-09-15 Impact factor: 15.419

7. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors: Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal: J Am Chem Soc Date: 2008-06-27 Impact factor: 15.419

8. Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.

Authors: David R Stuart; Elisia Villemure; Keith Fagnou
Journal: J Am Chem Soc Date: 2007-09-19 Impact factor: 15.419

Review 9. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Authors: Shannon S Stahl
Journal: Angew Chem Int Ed Engl Date: 2004-06-28 Impact factor: 15.336

10. The catalytic cross-coupling of unactivated arenes.

Authors: David R Stuart; Keith Fagnou
Journal: Science Date: 2007-05-25 Impact factor: 47.728

24 in total

1. Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).

Authors: Alison N Campbell; Shannon S Stahl
Journal: Acc Chem Res Date: 2012-01-23 Impact factor: 22.384

2. A general method for copper-catalyzed arene cross-dimerization.

Authors: Hien-Quang Do; Olafs Daugulis
Journal: J Am Chem Soc Date: 2011-08-08 Impact factor: 15.419

3. Palladium-Catalyzed Aerobic Acetoxylation of Benzene using NO_x-Based Redox Mediators.

Authors: Susan L Zultanski; Shannon S Stahl
Journal: J Organomet Chem Date: 2015-05-01 Impact factor: 2.369

4. 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

5. Can Donor Ligands Make Pd(OAc)₂ a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria.

Authors: David L Bruns; Djamaladdin G Musaev; Shannon S Stahl
Journal: J Am Chem Soc Date: 2020-11-09 Impact factor: 15.419

6. Mechanistic Basis for Efficient, Site-Selective, Aerobic Catalytic Turnover in Pd-Catalyzed C-H Imidoylation of Heterocycle-Containing Molecules.

Authors: Stephen J Tereniak; Shannon S Stahl
Journal: J Am Chem Soc Date: 2017-10-06 Impact factor: 15.419