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Laccase-Catalyzed C[BOND]S and C[BOND]C Coupling for a One-Pot Synthesis of 1,4-Naphthoquinone Sulfides and 1,4-Naphthoquinone Sulfide Dimers

Authors

  • Dr. Kevin W. Wellington,

    Corresponding author
    1. Council for Scientific and Industrial Research (CSIR), CSIR Biosciences, P O Box 395, Pretoria, Gauteng (South Africa), Fax: (+27) 12 841 3388
    • Council for Scientific and Industrial Research (CSIR), CSIR Biosciences, P O Box 395, Pretoria, Gauteng (South Africa), Fax: (+27) 12 841 3388
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  • Dr. Gregory E. R. Gordon,

    1. Council for Scientific and Industrial Research (CSIR), CSIR Biosciences, P O Box 395, Pretoria, Gauteng (South Africa), Fax: (+27) 12 841 3388
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  • Lindelani A. Ndlovu,

    1. Council for Scientific and Industrial Research (CSIR), CSIR Biosciences, P O Box 395, Pretoria, Gauteng (South Africa), Fax: (+27) 12 841 3388
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  • Prof. Paul Steenkamp

    1. Council for Scientific and Industrial Research (CSIR), CSIR Biosciences, P O Box 395, Pretoria, Gauteng (South Africa), Fax: (+27) 12 841 3388
    2. Department of Biochemistry, University of Johannesburg, PO Box 524, Auckland Park, 2006 (South Africa)
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Abstract

Oxidative C[BOND]S and C[BOND]C bond formation with aryl and alkyl thiols was catalyzed under mild conditions in a reaction vessel open to air at pH 4.5 in the presence of a commercial laccase (Novozym 51003 or Suberase) and a cosolvent (DMF) to afford 1,4-naphthoquinone sulfides. Although both monothiolation and dithiolation of the 1,4-naphthohydroquinone were accomplished, the latter was favored. In addition, unprecedented dimerization of monothiolated intermediates occurred through C[BOND]C coupling. These commercial laccases provide a facile and a more environmentally friendly synthetic approach to both 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers.

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