Literature DB >> 25843978

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

Susan L Zultanski1, Shannon S Stahl1.   

Abstract

Palladium-catalyzed methods for C-H oxygenation with O2 as the stoichiometric oxidant are limited. Here, we describe the use of nitrite and nitrate sources as NOx-based redox mediators in the acetoxylation of benzene. The conditions completely avoid formation of biphenyl as a side product, and strongly favor formation of phenyl acetate over nitrobenzene (PhOAc:PhNO2 ratios up to 40:1). Under the optimized reaction conditions, with 0.1 mol% Pd(OAc)2, 136 turnovers of Pd are achieved with only 1 atm of O2 pressure.

Entities:  

Keywords:  C–H activation; aerobic; benzene; nitrate; nitric acid; nitrite; oxidation; palladium; phenol; phenyl acetate; redox mediators

Year:  2015        PMID： 25843978      PMCID： PMC4379509          DOI： 10.1016/j.jorganchem.2015.03.003

Source DB:  PubMed          Journal:  J Organomet Chem        ISSN： 0022-328X            Impact factor:   2.369


  22 in total

1.  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

2.  Steric control of site selectivity in the Pd-catalyzed C-H acetoxylation of simple arenes.

Authors:  Amanda K Cook; Marion H Emmert; Melanie S Sanford
Journal:  Org Lett       Date:  2013-10-14       Impact factor: 6.005

3.  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

4.  Nitrate as a Redox Co-Catalyst for the Aerobic Pd-Catalyzed Oxidation of Unactivated sp(3)-C-H Bonds.

Authors:  Kara J Stowers; Asako Kubota; Melanie S Sanford
Journal:  Chem Sci       Date:  2012-08-30       Impact factor: 9.825

5.  tert-Butyl nitrite mediated regiospecific nitration of (E)-azoarenes through palladium-catalyzed directed C-H activation.

Authors:  Biju Majhi; Debasish Kundu; Sabir Ahammed; Brindaban C Ranu
Journal:  Chemistry       Date:  2014-07-10       Impact factor: 5.236

6.  The aerobic oxidation of a Pd(II) dimethyl complex leads to selective ethane elimination from a Pd(III) intermediate.

Authors:  Julia R Khusnutdinova; Nigam P Rath; Liviu M Mirica
Journal:  J Am Chem Soc       Date:  2012-01-20       Impact factor: 15.419

7.  Bimetallic redox synergy in oxidative palladium catalysis.

Authors:  David C Powers; Tobias Ritter
Journal:  Acc Chem Res       Date:  2011-10-27       Impact factor: 22.384

8.  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

9.  Catalytic aerobic oxidation of substituted 8-methylquinolines in Pd(II)-2,6-pyridinedicarboxylic acid systems.

Authors:  Jing Zhang; Eugene Khaskin; Nicholas P Anderson; Peter Y Zavalij; Andrei N Vedernikov
Journal:  Chem Commun (Camb)       Date:  2008-06-16       Impact factor: 6.222

10.  High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

Authors:  Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  5 in total

1.  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

2.  High-Potential Electrocatalytic O2 Reduction with Nitroxyl/NO x Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis.

Authors:  James B Gerken; Shannon S Stahl
Journal:  ACS Cent Sci       Date:  2015-07-15       Impact factor: 14.553

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

Authors:  Fanji Kong; Shusen Chen; Junqi Chen; Chang Liu; Weihao Zhu; Diane A Dickie; William L Schinski; Sen Zhang; Daniel H Ess; T Brent Gunnoe
Journal:  Sci Adv       Date:  2022-08-24       Impact factor: 14.957

4.  Carboxylate-assisted C-H activation of phenylpyridines with copper, palladium and ruthenium: a mass spectrometry and DFT study.

Authors:  A Gray; A Tsybizova; J Roithova
Journal:  Chem Sci       Date:  2015-07-01       Impact factor: 9.825

Review 5.  Efficient Aerobic Oxidation of Organic Molecules by Multistep Electron Transfer.

Authors:  Jie Liu; Arnar Guðmundsson; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-24       Impact factor: 16.823
  5 in total

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