Premium
Laccase‐Catalyzed CS and CC Coupling for a One‐Pot Synthesis of 1,4‐Naphthoquinone Sulfides and 1,4‐Naphthoquinone Sulfide Dimers
Author(s) -
Wellington Kevin W.,
Gordon Gregory E. R.,
Ndlovu Lindelani A.,
Steenkamp Paul
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200606
Subject(s) - chemistry , 1,4 naphthoquinone , naphthoquinone , catalysis , sulfide , dimethyl sulfide , aryl , laccase , oxidative coupling of methane , organic chemistry , medicinal chemistry , alkyl , combinatorial chemistry , sulfur , enzyme
Oxidative CS and CC 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 CC 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.