Categories: S-H Bond Formation >
Reduction of sulfoxides
Recent Literature
Sodium borohydride in the presence of iodine in anhydrous THF converts
various sulfoxides to their thioethers in excellent yields. A chemoselective
deoxygenation of sulfoxides can be achieved in the presence of other
reducible functional groups such as esters, nitriles and double bonds.
B. Karimi, D. Zareyee, Synthesis, 2003, 335-336.
A dichlorodioxomolybdenum(VI)-catalyzed oxotransfer allows a chemoselective
deoxygenation of sulfoxides to sulfides in the presence of P(OPh)3 as
the stoichiometric reductant.
R. Sanz, J. Escribano, R. Aguado, M. R. Pedrosa, F. J. Arnáiz, Synthesis, 2004,
1629-1632.
Various alkyl and aryl sulfoxides have been successfully deoxygenated using
3-mercaptopropionic acid as a reducing agent and a catalytic amount of
either NBS or I2 in MeCN at ambient temperature. Under the
described reaction conditions, acid sensitive substrates such as acetals
remained intact.
B. Karimi, D. Zareyee, Synthesis, 2003, 1875-1877.
Sulfoxides and aza-aromatic N-oxides were deoxygenated using a system
of indium and pivaloyl chloride at room temperature to give the
corresponding sulfides and aza-aromatics in high yields.
E. S. Park, S. Hwan, Lee, J. H. Lee, H. J. Rhee, C. M. Yoon, Synthesis, 2005, 3499-3501.
