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Synthesis of quinolinequinone derivatives and related carbocyclic compounds

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      Abstract

      Palladium-catalyzed Buchwald-Hartwig aminations of various quinolinequinone derivatives give excellent yields of novel 6-arylamino derivatives of the disubstituted quinolinequinones and 3-arylamino derivatives of the corresponding naphthoquinones. The precursor quinolinequinones are prepared in a three-step sequence from 8-hydroxyquinoline. The transition-metal-catalyzed arylations of 6,7-dibromo-5,8-quinolinequinone, 6,7-dichloro-5,8-quinolinequinone and 2,3-dichloro-1,4-naphthoquinone are reported for the first time and offer fast and easy access to their derivatives.

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      Most cited references 14

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      Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions.

      The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been significantly expanded to include aryl halides containing primary amides and free carboxylic acid groups. In the case of multifunctional substrates, the Pd-catalyzed amination can provide selectivity that is complementary to the Cu-catalyzed C-N bond-forming processes.
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        Palladium-catalyzed formation of carbon-nitrogen bonds. Reaction intermediates and catalyst improvements in the hetero cross-coupling of aryl halides and tin amides

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          Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation.

          Bulky biaryl phosphine ligands facilitate Pd-catalyzed C-O coupling reactions of aryl halides with primary and secondary alcohols by promoting reductive elimination at the expense of beta-hydride elimination. The key to their success is the ability to match the size of the ligand to that of the combination of substrates. The efficient coupling of a number of unactivated aryl chlorides and bromides with cyclic and acyclic secondary alcohols was achieved. This included the coupling of allylic alcohols for the first time in a Pd-catalyzed coupling process.
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            Author and article information

            Affiliations
            [1 ]Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
            [2 ]School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff CF10 3AT, UK
            Author notes
            [* ]Corresponding author's e-mail address: wirth@ 123456cf.ac.uk
            Contributors
            Journal
            SOR-CHEM
            ScienceOpen Research
            ScienceOpen
            2199-1006
            19 December 2014
            : 0 (ID: 4e3315b4-59e4-49b2-b49e-078ceb9cce92 )
            : 0
            : 1-6
            2302:XE
            10.14293/S2199-1006.1.SOR-CHEM.AALL9P.v1
            © 2014 S.A. Egu et al.

            This work has been published open access under Creative Commons Attribution License CC BY 4.0 , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Conditions, terms of use and publishing policy can be found at www.scienceopen.com .

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            Figures: 14, Tables: 3, References: 16, Pages: 6
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            Original article

            Chemistry

            Pd catalysis, amination, quinolidinequinones, Buchwald-Hartwig reaction

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