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Dr. Kevin W. Wellington, Dr. Gregory E. R. Gordon, Lindelani A. Ndlovu and Prof. Paul Steenkamp 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 ChemCatChem 5

Version of Record online: 1 MAR 2013 | DOI: 10.1002/cctc.201200606

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A beautiful couple: Oxidative C[BOND]S and C[BOND]C bond formation with aryl and alkyl thiols is 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 are accomplished, the latter is favored.

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