Literature DB >> 21851123

Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones.

Tianning Diao1, Shannon S Stahl.   

Abstract

α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)(2)(TFA)(2) as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O(2) as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.

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Year:  2011        PMID： 21851123      PMCID： PMC3173566          DOI： 10.1021/ja206575j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  32 in total

1.  11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

Authors:  Seth B Herzon; Liang Lu; Christina M Woo; Shivajirao L Gholap
Journal:  J Am Chem Soc       Date:  2011-01-31       Impact factor: 15.419

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

Review 3.  Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.

Authors:  Graham E Dobereiner; Robert H Crabtree
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

4.  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

5.  Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols.

Authors:  Yusuke Izawa; Doris Pun; Shannon S Stahl
Journal:  Science       Date:  2011-06-09       Impact factor: 47.728

6.  Palladium(II)-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones by Molecular Oxygen.

Authors:  Takahiro Nishimura; Tomoaki Onoue; Kouichi Ohe; Sakae Uemura
Journal:  J Org Chem       Date:  1999-09-03       Impact factor: 4.354

7.  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

Review 8.  The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms.

Authors:  Rainer Cermak; Siegfried Wolffram
Journal:  Curr Drug Metab       Date:  2006-10       Impact factor: 3.731

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.  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
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  54 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.  Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

Authors:  Hem Raj Khatri; Bijay Bhattarai; Will Kaplan; Zhongzheng Li; Marcus John Curtis Long; Yimon Aye; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2019-03-14       Impact factor: 15.419

3.  Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products.

Authors:  Andrei V Iosub; Shannon S Stahl
Journal:  ACS Catal       Date:  2016-10-24       Impact factor: 13.084

4.  Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion.

Authors:  Alexander W Schuppe; Yizhou Zhao; Yannan Liu; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2019-06-03       Impact factor: 15.419

5.  Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand.

Authors:  Tyler J Fulton; Brenda Wu; Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal:  Tetrahedron       Date:  2019-06-01       Impact factor: 2.457

6.  Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP.

Authors:  Yang Yu; Ranad Humeidi; James R Alleyn; Michael P Doyle
Journal:  J Org Chem       Date:  2017-08-04       Impact factor: 4.354

7.  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

8.  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

9.  Terminal olefins to linear α,β-unsaturated ketones: Pd(II)/hypervalent iodine co-catalyzed Wacker oxidation-dehydrogenation.

Authors:  Marinus A Bigi; M Christina White
Journal:  J Am Chem Soc       Date:  2013-05-17       Impact factor: 15.419

10.  Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon.

Authors:  Andrei V Iosub; Shannon S Stahl
Journal:  Org Lett       Date:  2015-09-02       Impact factor: 6.005
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