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Synthesis of sulfoxides
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Synthesis of sulfoxides |
Recent Literature
An excellent method for the selective oxidation of sulfides to sulfoxides
with periodic acid (H5IO6) catalyzed by FeCl3
in MeCN has been devised. The reported procedure is fast, simple and the
yields are excellent in most cases with reaction time of less than 2 minutes.
S. S. Kim, K. Nehru, S. S. Kim, D. W. Kim, H. C. Jung, Synthesis, 2002, 2484-2486.
A mild, efficient and environmentally friendly oxidation of sulfides to
sulfoxides with a recyclable ion-supported hypervalent iodine reagent tolerates
hydroxyl, nitrile, methoxy, carbon-carbon double bonds, and ester
functionalities. Aliphatic and aromatic sulfides are selectively oxidized to the
corresponding sulfoxides at room temperature in excellent yields without
over-oxidation.
W. Qian, L. Pei, Synlett,
2006, 709-712.
Sc(OTf)3 is an efficient catalyst for the hydrogen peroxide mediated
monooxidation of alkyl-aryl sulfides and methyl cysteine containing peptides.
The method is high yielding, compatible with many widely used protecting groups,
suitable for solid-phase applications and proceeds with minimum over-oxidation.
M. Matteucci, G. Bhalay, M. Bradley, Org. Lett., 2003, 5,
235-237.
An air and moisture tolerant complex of Ti(IV) with a C3-symmetric
triphenolate amine ligand efficiently catalyzes sulfoxidation reactions at room
temperature without previous activation using aqueous hydrogen peroxide as
oxidant.
M. Mba, l. J. Prins, G. Licini, Org. Lett., 2007,
9, 21-24.
The combination of very high ee values with high yield, the consequence of
an efficient initial asymmetric oxidation followed by an efficient kinetic
resolution, makes the reported system very practical for the asymmetric
oxidation of simple akyl aryl sulfides.
C. Drago, L. Caggiano, R. F. W. Jackson, Angew. Chem., 2005, 117, 7387-7389.
The asymmetric oxidation of sulfides to chiral
sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has
been catalyzed very effectively by a chiral vanadium-salan complex. The efficient kinetic resolution of racemic
sulfoxides catalyzed by the vanadium-salan system is also described.
J. Sun, C. Zhu, Z. Dai, M. Xang, Y. Pan, H. Hu, J. Org. Chem.,
2004, 69, 8500-8503.
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.
Oxidations of organic substrates such as sulfides, secondary amines, N-hydroxylamines,
and tertiary amines with molecular oxygen in the presence of
5-ethyl-3-methyllumiflavinium perchlorate catalyst and hydrazine monohydrate
in 2,2,2-trifluoroethanol occur highly efficiently to give the corresponding
oxidized compounds in excellent yields.
Y. Imada, H. Iida, S. Ono, S.-I. Murahashi, J. Am. Chem. Soc., 2003, 125, 2868-2869.
Urea-hydrogen peroxide adduct (UHP) is stable, inexpensive and an easily handled
reagent. UHP 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.
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Enantioselective Sulfoxidation |
