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Literature DB >> 21860880

Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands.

Alison N Campbell¹, Eric B Meyer, Shannon S Stahl.

Abstract

Palladium-catalyzed aerobic oxidative cross-couplings of indoles and benzene have been achieved by using 4,5-diazafluorene derivatives as ancillary ligands. Proper choice of the neutral and anionic ligands enables control over the reaction regioselectivity. This journal is © The Royal Society of Chemistry 2011

Entities: Chemical Gene

Mesh：

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Year: 2011 PMID： 21860880 PMCID： PMC3228523 DOI： 10.1039/c1cc13632a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

31 in total

1. Oxygenation of nitrogen-coordinated palladium(0): synthetic, structural, and mechanistic studies and implications for aerobic oxidation catalysis.

Authors: S S Stahl; J L Thorman; R C Nelson; M A Kozee
Journal: J Am Chem Soc Date: 2001-07-25 Impact factor: 15.419

2. Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.

Authors: Alison N Campbell; Paul B White; Ilia A Guzei; Shannon S Stahl
Journal: J Am Chem Soc Date: 2010-11-03 Impact factor: 15.419

3. 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

4. Regioselective oxidative arylation of indoles bearing N-alkyl protecting groups: dual C-H functionalization via a concerted metalation-deprotonation mechanism.

Authors: Shathaverdhan Potavathri; Kyle C Pereira; Serge I Gorelsky; Andrew Pike; Alexis P LeBris; Brenton DeBoef
Journal: J Am Chem Soc Date: 2010-10-20 Impact factor: 15.419

5. Palladium-catalyzed oxidative cross-coupling between pyridine N-oxides and indoles.

Authors: Xue Gong; Guoyong Song; Hong Zhang; Xingwei Li
Journal: Org Lett Date: 2011-03-09 Impact factor: 6.005

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

7. 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 8. 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

9. Reaction of molecular oxygen with a Pd(II)-hydride to produce a Pd(II)-hydroperoxide: experimental evidence for an HX-reductive-elimination pathway.

Authors: Michael M Konnick; Shannon S Stahl
Journal: J Am Chem Soc Date: 2008-04-05 Impact factor: 15.419

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors: Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

23 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. Base-Assisted C-H Bond Cleavage in Cross-Coupling: Recent Insights into Mechanism, Speciation, and Cooperativity.

Authors: Brad P Carrow; Jessica Sampson; Long Wang
Journal: Isr J Chem Date: 2019-12-13 Impact factor: 3.333

3. 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

4. Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C-H Acetoxylation Catalyzed by Pd(OAc)₂/4,5-Diazafluoren-9-one.

Authors: Jonathan N Jaworski; Caitlin V Kozack; Stephen J Tereniak; Spring Melody M Knapp; Clark R Landis; Jeffrey T Miller; Shannon S Stahl
Journal: J Am Chem Soc Date: 2019-06-25 Impact factor: 15.419

5. Cobalt-promoted dimerization of aminoquinoline benzamides.

Authors: Liene Grigorjeva; Olafs Daugulis
Journal: Org Lett Date: 2015-02-17 Impact factor: 6.005

6. Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions.

Authors: Changwu Zheng; Dian Wang; Shannon S Stahl
Journal: J Am Chem Soc Date: 2012-09-28 Impact factor: 15.419

7. Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.

Authors: Paul B White; Jonathan N Jaworski; Geyunjian Harry Zhu; Shannon S Stahl
Journal: ACS Catal Date: 2016-03-11 Impact factor: 13.084

8. Structurally Diverse Diazafluorene-Ligated Palladium(II) Complexes and Their Implications for Aerobic Oxidation Reactions.

Authors: Paul B White; Jonathan N Jaworski; Charles G Fry; Brian S Dolinar; Ilia A Guzei; Shannon S Stahl
Journal: J Am Chem Soc Date: 2016-04-05 Impact factor: 15.419

9. Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

Authors: Yusuke Izawa; Changwu Zheng; Shannon S Stahl
Journal: Angew Chem Int Ed Engl Date: 2013-02-19 Impact factor: 15.336

Review 10. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors: Keary M Engle; Jin-Quan Yu
Journal: J Org Chem Date: 2013-05-03 Impact factor: 4.354