Literature DB >> 24623664

Aerobic double dehydrogenative cross coupling between cyclic saturated ketones and simple arenes.

Nicolas Gigant1, Jan-E Bäckvall.   

Abstract

The synthesis of 3-aryl-2-cyclohexenones is a topic of current interest as they are not only privileged structures in bioactive molecules, but they are also relevant feedstocks for the synthesis of substituted phenols or anilines, which are ubiquitous structural elements both in drug design and medicinal chemistry. A simple and sustainable one-pot aerobic double dehydrogenative reaction under mild conditions for the introduction of arenes in the β-position of cyclic ketones has been developed. Starting from the corresponding saturated ketone, this reaction sequence proceeds under relatively low Pd catalyst loading and involves catalytic amounts of electron-transfer mediators (ETMs) under ambient oxygen pressure.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; aerobic oxidation; biomimetic cross-coupling; double dehydrogenation; synthetic methods

Year:  2014        PMID: 24623664     DOI: 10.1002/chem.201402063

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 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

2.  Ligand-enabled triple C-H activation reactions: one-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides.

Authors:  Youqian Deng; Wei Gong; Jian He; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-14       Impact factor: 15.336

3.  Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

Authors:  Nicolas Gigant; François Quintin; Jan-E Bäckvall
Journal:  J Org Chem       Date:  2015-02-16       Impact factor: 4.354

  3 in total

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