Literature DB >> 30861346

Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones.

David Huang1, Suzanne M Szewczyk1, Pengpeng Zhang1, Timothy R Newhouse1.   

Abstract

We herein disclose the first report of a first-row transition metal-catalyzed α,β-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction that provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.

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Year:  2019        PMID： 30861346      PMCID： PMC7495923          DOI： 10.1021/jacs.9b02552

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


  27 in total

1.  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

Review 2.  Syntheses and applications of functionalized bicyclo[3.2.1]octanes: thirteen years of progress.

Authors:  Marc Presset; Yoann Coquerel; Jean Rodriguez
Journal:  Chem Rev       Date:  2012-10-19       Impact factor: 60.622

Review 3.  Domino reactions for the synthesis of bridged bicyclic frameworks: fast access to bicyclo[n.3.1]alkanes.

Authors:  Miriam Ruiz; Pilar López-Alvarado; Giorgio Giorgi; J Carlos Menéndez
Journal:  Chem Soc Rev       Date:  2011-04-11       Impact factor: 54.564

4.  On the remarkably different role of salt in the cross-coupling of arylzincs from that seen with alkylzincs.

Authors:  Lucas C McCann; Michael G Organ
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-26       Impact factor: 15.336

5.  Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation.

Authors:  David Huang; Yizhou Zhao; Timothy R Newhouse
Journal:  Org Lett       Date:  2018-01-12       Impact factor: 6.005

6.  Allyl-Palladium-Catalyzed α,β-Dehydrogenation of Carboxylic Acids via Enediolates.

Authors:  Yizhou Zhao; Yifeng Chen; Timothy R Newhouse
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-06       Impact factor: 15.336

7.  Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization.

Authors:  Ming Chen; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2017-06-06       Impact factor: 15.419

8.  Palladium- and nickel-catalyzed alkenylation of enolates.

Authors:  Tobias Ankner; Casey C Cosner; Paul Helquist
Journal:  Chemistry       Date:  2013-01-16       Impact factor: 5.236

9.  Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles.

Authors:  Yifeng Chen; Justin P Romaire; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2015-04-28       Impact factor: 15.419

10.  Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide.

Authors:  Yifeng Chen; Aneta Turlik; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2016-01-21       Impact factor: 15.419
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  2 in total

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Authors:  David Huang; Timothy R Newhouse
Journal:  Acc Chem Res       Date:  2021-02-16       Impact factor: 22.384

2.  Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light.

Authors:  Wan-Lei Yu; Zi-Gang Ren; Ke-Xing Ma; Hui-Qing Yang; Jun-Jie Yang; Haixue Zheng; Wangsuo Wu; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-06-15       Impact factor: 9.969
  2 in total

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