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Manganese-Catalyzed Selective Oxidation of Aliphatic C[BOND]H groups and Secondary Alcohols to Ketones with Hydrogen Peroxide

Authors

  • Jia Jia Dong,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Duenpen Unjaroen,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Francesco Mecozzi,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Dr. Emma C. Harvey,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Dr. Pattama Saisaha,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Dr. Dirk Pijper,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Dr. Johannes W. de Boer,

    1. Catexel BV BioPartner Center Leiden, Galileiweg 8, 2333 BD Leiden (The Netherlands)
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  • Dr. Paul Alsters,

    1. DSM Innovative Synthesis, PO Box 18, 6160 MD Geleen (The Netherlands)
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  • Prof. Dr. Ben L. Feringa,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Prof. Dr. Wesley R. Browne

    Corresponding author
    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296
    • Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands), Fax: (+31) 50-363-4296

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Abstract

An efficient and simple method for selective oxidation of secondary alcohols and oxidation of alkanes to ketones is reported. An in situ prepared catalyst is employed based on manganese(II) salts, pyridine-2-carboxylic acid, and butanedione, which provides good-to-excellent conversions and yields with high turnover numbers (up to 10 000) with H2O2 as oxidant at ambient temperatures. In substrates bearing multiple alcohol groups, secondary alcohols are converted to ketones selectively and, in general, benzyl C[BOND]H oxidation proceeds in preference to aliphatic C[BOND]H oxidation.

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