Erratum to: Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant

Research on Chemical Intermediates -     

1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane as new oxidant for chemoselective and catalyst free oxidation of sulfides to sulfoxides and sulfones

A catalyst free and chemoselective oxidation of sulfides to sulfoxides or sulfones was developed using 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as a new oxidant. This scope has shown the achievement of various sulfoxides and sulfones which were obtained selectively in high yields at room temperature.     

Selective oxidation of sulfides to sulfoxides and sulfones using 30% aqueous hydrogen peroxide and silica-vanadia catalyst

A green, efficient and selective approach for the oxidation of sulfides to sulfoxides and sulfones with stoichiometric amount of 30% aq. H₂O₂ is reported. The reaction is performed in methanol with silica-vanadia as heterogeneous and reusable catalyst.     

Highly efficient oxidation of alcohols using Oxone as oxidant catalyzed by ruthenium complex under mild reaction conditions

Aromatic and alkyl alcohols were oxidized to the corresponding aldehydes or ketones at room temperature with high conversion and selectivity using Oxone （2KHSOs-KHSO4.K2SO4） as oxidant catalyzed by ruthenium complex Quin-Ru-Quin （where Quin = 8-hydroxyquinoline）. The reaction time is very short and the preparation of complex is simple.     

Copper catalyzed oxidation of sulfides to sulfoxides with aqueous hydrogen peroxide

Copper(II) complex 1 catalyzes the oxidation of sulfides to sulfoxides with 30% H₂O₂ in high yields. Addition of a catalytic amount of TEMPO to the reaction mixture enhances the conversion and selectivity. Complex 1 can be recycled without loss of activity.     

Selective aerobic oxidation of sulfides to sulfoxides catalyzed by coenzyme NAD models

Coenzyme NAD⁺ models can be applied in the photooxygenation of sulfides to sulfoxides as organocatalysts at room temperature. A series of sulfoxides are synthesized easily with this protocol and the possible mechanism is discussed. This procedure provides a reliable approach to the clean production of useful sulfoxides in synthetic chemistry.     

Selective synthesis of sulfoxides and sulfones by tantalum(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide

The reaction of sulfides with 30% hydrogen peroxide catalyzed by tantalum(V) chloride in acetonitrile, i-propanol, or t-butanol selectively provided the corresponding sulfoxides in high yields. On the other hand, the reaction of sulfides with 30% hydrogen peroxide-catalyzed by tantalum(V) chloride or tantalum(V) ethoxide in methanol effectively gave the sulfones.     

Gold(III) catalyzed oxidation of sulfides to sulfoxides with hydrogen peroxide

Au(III) catalyzed oxidation of sulfides to sulfoxides with 30% hydrogen peroxide in good yields and chemoselectivities was developed. It was shown that the catalyst loading can be decreased to 0.01 mol % with the good activity and chemoselectivity. Meanwhile, the catalyst was stable in the reaction system, which can be reused at least six cycles with similar activity and chemoselectivity.     

Safe oxidation of sulfides into sulfoxides using SIBX

SIBX is a stabilized (i.e., nonexplosive) formulation of the λ⁵-iodane 2-iodoxybenzoic acid IBX that can be used as a suspension in various organic solvents to oxidize safely sulfides into sulfoxides. Most yields are comparable to those obtained using IBX or other iodanes such as PhIO and PhIO₂. An asymmetric version of this SIBX-mediated sulfoxidation was performed in high chemical yield and moderate enantioselectivity by simple addition of an external chiral source.     

From vinyl sulfides, sulfoxides and sulfones to vinyl zirconocene derivatives

An easy and straightforward new method for the preparation of sp² zirconocene derivatives from a wide range of heterosubstituted alkenes such as vinyl sulfides, sulfoxides and sulfones is described. In all cases, a complete isomerization of the stereochemistry is observed and only the E-isomer is obtained. The reactivity of the resulting vinylic organometallic can be increased by a transmetalation reaction into organocopper, organozinc or organopalladium species and, therefore, several carbon-carbon formation were easily realized.     

Highly efficient oxidation of alcohols using Oxone(R) as oxidant catalyzed by ruthenium complex under mild reaction conditions

Aromatic and alkyl alcohols were oxidized to the corresponding aldehydes or ketones at room temperature with high conversion and selectivity using Oxone (2KHSO5·KHSO4·K2SO4) as oxidant catalyzed by ruthenium complex Quin-Ru-Quin (where Quin = 8-hydroxyquinoline). The reaction time is very short and the preparation of complex is simple. 2008 Zi Qiang Lei. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid

A highly efficient and selective oxidation of sulfides to sulfones with periodic acid catalyzed by CrO(3) is described. A variety of electron-rich and electron-deficient sulfides were oxidized to sulfones with 2 mol % CrO(3) 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 % CrO(3) in ethyl acetate/acetonitrile at -35 degrees C.     

Controllable oxidation of sulfides to sulfoxides and sulfones with aqueous hydrogen peroxide in the presence of β-cyclodextrin

A facile procedure has been developed for the transition metal-free oxidation of sulfides to sulfoxides and sulfones and of sulfoxides to sulfones with hydrogen peroxide in aqueous medium in the presence of β-cyclodextrin as catalyst. The procedure allows formation of sulfoxide or sulfone to be controlled. Published in Russian in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 979–981. The original text was submitted by the authors in English.     

An efficient asymmetric oxidation of sulfides to sulfoxides

The Sharpless reagent (Ti(OiPr)₄ + 1 mol eq. diethyl tartrate (DET) + 2 t-BuOOH) modified by addition of one mol eq. H₂O gives a new homogeneous reagent which cleanly oxidizes sulfides into sulfoxides in dichloromethane. The best results were obtained for the stoichiometry Ti/DET/H₂O/t-BuOOH = 1:2:1:2. The e.e. observed ranged from 4 to 93% with the highest beeing observed in the case of methyl p-toly] sulfoxide.     

Selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide catalyzed with a recoverable silica-based tungstate interphase catalyst

Various types of aromatic and aliphatic sulfides are selectively oxidized to sulfoxides and sulfones in good to excellent yields using 30% H2O2 in the presence of catalytic amounts of a novel recoverable silica-based tungstate interphase catalyst at room temperature. The catalyst can be recovered and reused for at least eight reaction cycles under the described reaction conditions without considerable loss of reactivity. [reaction: see text]     

Selective oxidation of glycosyl sulfides to sulfoxides using magnesium monoperoxyphthalate and microwave irradiation

A protocol that uses moist magnesium monoperoxyphthalate (MMPP) as an oxidant under microwave irradiation rapidly yields a variety of glycosyl sulfoxides from corresponding sulfides in high yields with high selectivity.     

Fe3O4 as a magnetically reusable Fenton nanocatalyst for the oxidation of thiols to sulfonic acid and sulfides to sulfoxides and sulfones

In this study, the oxidation of thiols to sulfonic acids and sulfides to sulfoxides and sulfones was carried out in the presence of Fe₃O₄/H₂O₂ as an efficient heterogeneous Fenton system. The products were obtained in good to excellent yields and short reaction times. Further results showed that the heterogeneous catalyst could be recovered easily using an external magnetic field and reused several times without any loss of its catalytic activity.     

A mild,chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as catalyst

A mild, selective, and high-yielding method for oxidation of sulfides to sulfoxides using IBX and tetraethylammonium bromide in a variety of solvents is described. The method offers the advantage of short reaction times, no over-oxidation to sulfones, and compatibility to a wide range of functional groups.