Literature DB >> 19662234

Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Keith M Gligorich1, Matthew S Sigman.   

Abstract

During the past 10 years there have been significant advances in Pd(II)-catalyzed oxidation reactions where the use of ligands has led to the development of catalytic systems capable of achieving high turnover numbers, which employ molecular oxygen as the sole stoichiometric oxidant. This Feature article will highlight some of the recent developments in direct molecular oxygen-coupled Pd(II)-catalyzed oxidation reactions with an emphasis on enhanced catalytic systems and new reactions. Additionally, limitations of current catalytic systems, such as ligand oxidation, are presented and their implications for the development of new reactions are discussed.

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Year:  2009        PMID: 19662234      PMCID: PMC2873851          DOI: 10.1039/b902868d

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


  71 in total

1.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors:  Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  Chemistry. Palladium-catalyzed oxidation of organic chemicals with O2.

Authors:  Shannon S Stahl
Journal:  Science       Date:  2005-09-16       Impact factor: 47.728

3.  Mechanism of Pd(OAc)2/DMSO-catalyzed aerobic alcohol oxidation: mass-transfer-limitation effects and catalyst decomposition pathways.

Authors:  Bradley A Steinhoff; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2006-04-05       Impact factor: 15.419

4.  Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.

Authors:  Kyung Soo Yoo; Cheol Hwan Yoon; Rajesh K Mishra; Young Chun Jung; Sung Wook Yi; Kyung Woon Jung
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

5.  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

6.  An experimentally derived model for stereoselectivity in the aerobic oxidative kinetic resolution of secondary alcohols by (sparteine)PdCl2.

Authors:  Raissa M Trend; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-04-14       Impact factor: 15.419

7.  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

8.  Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.

Authors:  Matthew S Sigman; David R Jensen
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384

9.  Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating.

Authors:  Jonas Lindh; Per-Anders Enquist; Ake Pilotti; Peter Nilsson; Mats Larhed
Journal:  J Org Chem       Date:  2007-09-21       Impact factor: 4.354

Review 10.  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

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  40 in total

1.  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

2.  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

3.  Catalytic asymmetric synthesis of chiral allylic esters.

Authors:  Stefan F Kirsch; Larry E Overman
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

4.  Detection of Palladium(I) in Aerobic Oxidation Catalysis.

Authors:  Jonathan N Jaworski; Scott D McCann; Ilia A Guzei; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-20       Impact factor: 15.336

5.  O2-Promoted Allylic Acetoxylation of Alkenes: Assessment of "Push" vs. "Pull" Mechanisms and Comparison between O2 and Benzoquinone.

Authors:  Tianning Diao; Shannon S Stahl
Journal:  Polyhedron       Date:  2014-12-14       Impact factor: 3.052

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

7.  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

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

Authors:  Alison N Campbell; Eric B Meyer; Shannon S Stahl
Journal:  Chem Commun (Camb)       Date:  2011-08-22       Impact factor: 6.222

9.  Characterization of DMSO coordination to palladium(II) in solution and insights into the aerobic oxidation catalyst, Pd(DMSO)2(TFA)2.

Authors:  Tianning Diao; Paul White; Ilia Guzei; Shannon S Stahl
Journal:  Inorg Chem       Date:  2012-10-23       Impact factor: 5.165

10.  Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose.

Authors:  Pengfei Zhang; Yutong Gong; Haoran Li; Zhirong Chen; Yong Wang
Journal:  Nat Commun       Date:  2013       Impact factor: 14.919

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