Categories: S=O Bond Formation >
Synthesis of sulfones
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Oxidation of sulfides with 30% hydrogen peroxide catalyzed by tantalum carbide
provides the corresponding sulfoxides in high yields, whereas niobium carbide as
catalyst efficiently affords the corresponding sulfones. Both catalysts can
easily be recovered and reused without losing their activity.
M. Kirihara, A. Itou, T. Noguchi, J. Yamamoto, Synlett, 2010,
1557-1561.

Urea-hydrogen peroxide adduct is
stable, inexpensive and an easily handled reagent. This reagent is used in an
efficient solid state oxidation of different organic molecules: hydroxylated
aldehydes and ketones (to hydroxylated phenols), sulfides (to sulfoxides and
sulfones), nitriles (to amides) and nitrogen heterocycles (to N-oxides).
R. S. Varma, K. P. Naicker, Org. Lett., 1999, 1,
189-191.

1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6-tetrachloride (TAPC) is an
efficient promoter for the oxidation of sulfides and deoxygenation of
sulfoxides. Excellent yields, short reaction time, easy and quick isolation of
the products, solvent-free process, and excellent chemoselectivity are the main
advantages of this procedure.
K. Bahrami, M. M. Khodaei, M. S. Arabi, J. Org. Chem., 2010,
75, 6208-6213.

K. Bahrami, M. M. Khodaei, M. S. Arabi, J. Org. Chem., 2010,
75, 6208-6213.

Use of a solvent with greater density than the fluorous phase is an alternative to the U-tube method in phase-vanishing reactions
in cases where both reactants are less dense
than the fluorous phase.
N. K. Jana, J. G. Verkade, Org. Lett., 2003, 5,
3787-3790.

Various aromatic and aliphatic sulfides are
selectively oxidized to sulfoxides and sulfones in good to excellent yields
using 30% H2O2 in the presence of a recyclable silica-based tungstate interphase catalyst at room temperature.
B. Karimi, M. Ghoreishi-Nezhad, J. H. Clark, Org. Lett., 2005, 7, 625-628.

Permanganate supported on active manganese dioxide can
be used effectively for the oxidation of
arenes, alcohols and sulfides under heterogeneous
or solvent-free conditions.
A. Shaabania, P. Mirzaeia, S. Naderia, D. G. Leeb, Tetrahedron, 2004, 60, 11415-11420.

β-Piperidinoethylsulfides can be oxidized by m-chloroperbenzoic acid to
intermediates containing both N-oxide and sulfone functions. These
undergo a Cope-type elimination to a vinylsulfone that can be captured by amines
to afford β-aminoethylsulfones. The synthetic methodology developed can be
utilized in multiple-parallel format and has numerous potential applications in
medicinal chemistry.
R. J. Gruffin, A. Henderson, N. J. Curtin, A. Echalier, J. A. Endicott, I. R.
Hardcastle, D. R. Newell, M. E. M. Noble, L.-Z. Wang, B. T. Golding, J. Am. Chem. Soc., 2006,
128, 6012-6013.

The reaction of 1-(methylthio)acetone with different nitriles in the
presence of triflic anhydride gave 2-substituted
5-methyl-4-methylthio-1,3-oxazoles in good yield. The methylthio group at
the C4 position can easily be removed with Raney nickel. 4-Methylsulfonyl
derivatives were prepared by the oxidation of the MeS group with m-CPBA.
