15251-78-2Relevant articles and documents
Enantioselective Aromatic Sulfide Oxidation and Tandem Kinetic Resolution Using Aqueous H2O2 and Chiral Iron–Bis(oxazolinyl)bipyridine Catalysts
Jalba, Angela,Régnier, Noémie,Ollevier, Thierry
, p. 1628 - 1637 (2017/04/06)
An efficient method for the oxidation of aromatic sulfides has been developed by using aqueous H2O2, catalyzed by the in situ generated chiral Fe/6,6′-bis(4-isopropyloxazolin-2-yl)-2,2′-bipyridine (bipybox-iPr) complex. The corresponding sulfoxides were obtained with high enantioselectivities (up to 98.5:1.5 er) and in good yields (up to 61 %) when the mono-oxidation of the sulfides was performed in combination with the kinetic resolution of the sulfoxide into the sulfone.
Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid
Xu, Liang,Cheng, Jie,Trudell, Mark L.
, p. 5388 - 5391 (2007/10/03)
A highly efficient and selective oxidation of sulfides to sulfones with periodic acid catalyzed by CrO3 is described. A variety of electron-rich and electron-deficient sulfides were oxidized to sulfones with 2 mol% CrO3 in acetonitrile at room temperature in excellent yields. Sulfides with other readily oxidized functional groups were selectively oxidized to sulfones in high yields with 10 mol% CrO3 in ethyl acetate/acetonitrile at -35 °C.
Oxidation of Sulfur-Containing Compounds with HOF-CH3CN
Rozen, Shlomo,Bareket, Yifat
, p. 1457 - 1462 (2007/10/03)
The HOF-CH3CN complex, easily prepared by passing F2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. All types of sulfides have been oxidized to sulfones in excellent yields, in a few minutes at room temperature. The reaction proceeds through the formation of sulfoxides which at low temperatures of around -75°C could be isolated in good yields. It was demonstrated through a reaction with thianthrene 5-oxide (20) that HOF·CH3CN is strongly electrophilic in nature. Sulfides with an electron-depleted sulfur atom such as perfluoroalkyl or aryl sulfides, which could not be well oxidized by any other method, were also efficiently converted to the corresponding sulfones in minutes. Thiophenes are generally hard to oxidize to the corresponding S-dioxides since the conditions required by the orthodox oxidants encourage consecutive typical ene and diene reactions. HOF·CH3CN requires short reaction times and low temperatures, thus enabling the isolation of thiophene dioxides, some of which could not be made by any other way. It seems that apart from unprotected amines, other functional groups such as aromatic rings, ketones, hydroxyls, and ethers do not interfere, since the sulfur atom reacts considerably faster.