Literature DB >> 26273111

Reductive Cyclization of Halo-Ketones to Form 3-Hydroxy-2-Oxindoles via Palladium Catalyzed Hydrogenation: A Hydrogen-Mediated Grignard Addition.

Inji Shin1, Stephen D Ramgren1, Michael J Krische1.   

Abstract

The reductive cyclization of N-oxoacyl ortho-bromoanilides to form 3-hydroxy-2-oxindoles under the conditions of palladium catalyzed hydrogenation is described. This work may be viewed as a prelude to intermolecular hydrogen-mediated Grignard-type reductive couplings of organic halides with carbonyl compounds.

Entities:  

Keywords:  carbonyl addition; hydrogenation; hydroxyl oxindole; palladium; reductive coupling

Year:  2015        PMID： 26273111      PMCID： PMC4528639          DOI： 10.1016/j.tet.2015.05.085

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  17 in total

1.  Metal-mediated reductive hydrodehalogenation of organic halides.

Authors:  Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal:  Chem Rev       Date:  2002-11       Impact factor: 60.622

2.  Trifluoroacetic acid-promoted synthesis of 3-hydroxy, 3-amino and spirooxindoles from α-keto-N-anilides.

Authors:  Ioulia Gorokhovik; Luc Neuville; Jieping Zhu
Journal:  Org Lett       Date:  2011-09-29       Impact factor: 6.005

3.  Highly enantioselective direct reductive coupling of conjugated alkynes and alpha-ketoesters via rhodium-catalyzed asymmetric hydrogenation.

Authors:  Jong-Rock Kong; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

4.  Applied hydroformylation.

Authors:  Robert Franke; Detlef Selent; Armin Börner
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

5.  Metal-catalyzed reductive coupling reactions of organic halides with carbonyl-type compounds.

Authors:  Toni Moragas; Arkaitz Correa; Ruben Martin
Journal:  Chemistry       Date:  2014-06-06       Impact factor: 5.236

6.  Cationic palladium complex catalyzed highly enantioselective intramolecular addition of arylboronic acids to ketones. A convenient synthesis of optically active cycloalkanols.

Authors:  Guixia Liu; Xiyan Lu
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

7.  Synthesis of 3-hydroxyoxindoles by Pd-catalysed intramolecular nucleophilic addition of aryl halides to alpha-ketoamides.

Authors:  Yi-Xia Jia; Dmitry Katayev; E Peter Kündig
Journal:  Chem Commun (Camb)       Date:  2009-11-03       Impact factor: 6.222

8.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

9.  Palladium-catalyzed direct arylation of indoles with cyclohexanones.

Authors:  Shanping Chen; Yunfeng Liao; Feng Zhao; Hongrui Qi; Saiwen Liu; Guo-Jun Deng
Journal:  Org Lett       Date:  2014-03-05       Impact factor: 6.005

10.  Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones: insight into the ketone alpha-arylation and carbonyl-addition dichotomy. A new class of four-membered azapalladacycles.

Authors:  Daniel Solé; Lluís Vallverdú; Xavier Solans; Mercè Font-Bardía; Josep Bonjoch
Journal:  J Am Chem Soc       Date:  2003-02-12       Impact factor: 15.419
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  4 in total

1.  Vinyl Triflate-Aldehyde Reductive Coupling-Redox Isomerization Mediated by Formate: Rhodium-Catalyzed Ketone Synthesis in the Absence of Stoichiometric Metals.

Authors:  William G Shuler; Robert A Swyka; Tabitha T Schempp; Brian J Spinello; Michael J Krische
Journal:  Chemistry       Date:  2019-09-04       Impact factor: 5.236

2.  Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition.

Authors:  Robert A Swyka; Wandi Zhang; Jeffery Richardson; J Craig Ruble; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-29       Impact factor: 15.419

3.  Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate.

Authors:  Robert A Swyka; William G Shuler; Brian J Spinello; Wandi Zhang; Chunling Lan; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-04-18       Impact factor: 15.419

4.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  4 in total

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