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Relevant academic research and scientific papers

Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine

An efficient and practical catalytic method for the aerobic oxidative transformation of sulfides into sulfoxides, and thiols into disulfides with formic acid/TEA in the presence of a new, readily available, and stable flavin catalyst 5d is described. This journal is the Partner Organisations 2014.

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.

Synthesis of Sulfoxides by the Hydrogen Peroxide Induced Oxidation of Sulfides Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin: Scope and Chemoselectivity

The oxidation of sulfides with H2O2 catalyzed by iron tetrakis(pentafluorophenyl)porphyrin in EtOH is an efficient and chemoselective process. With a catalyst concentration 0.03-0.09% of that of the substrate, sulfoxides are obtained with yields generally around 90-95% of isolated product. With vinyl and allyl sulfides, no epoxidation is observed. With a catalyst concentration between 0.09% and 0.25% of that of the substrate, sulfones are obtained in almost quantitative yield and with the same high chemoselectivity observed in the synthesis of sulfoxides.

Mechanism of the oxidation of aromatic sulfides catalysed by a water soluble iron porphyrin

The oxygen atom transfer-electron transfer (ET) mechanistic dichotomy has been investigated in the oxidation of a number of aryl sulfides by H2O2 in acidic (pH 3) aqueous medium catalysed by the water soluble iron(III) porphyrin 5,10,15,20-tetraphenyl-21H,23H-porphine-p,p′,p″,p?-tetrasulfo nic acid iron(III) chloride (FeTPPSCl). Under these reaction conditions, the iron-oxo complex porphyrin radical cation, P+ Fe(IV)=O, should be the active oxidant. When the oxidation of a series of para-X substituted phenyl alkyl sulfides (X = OCH3, CH3, H, Br, CN) was studied the corresponding sulfoxides were the only observed product and the reaction yields as well as the reactivity were little influenced by the nature of X as well as by the bulkiness of the alkyl group. Labelling experiments using H2 18O or H218O2 clearly indicated that the oxygen atom in the sulfoxides comes exclusively from the oxidant. Moreover, no fragmentation products were observed in the oxidation of a benzyl phenyl sulfide whose radical cation is expected to undergo cleavage of the β C-H and C-S bonds. These results would seem to suggest a direct oxygen atom transfer from the iron-oxo complex to the sulfide. However, competitive experiments between thioanisole (E° = 1.49 V vs. NHE in H2O) and N,N-dimethylaniline (E° = 0.97 V vs. NHE in H2O) resulted in exclusive N-demethylation, whereas the oxidation of N-methylphenothiazine (10, E° = 0.95 V vs. NHE in CH3CN) and N,N-dimethyl-4-methylthioaniline (11, E° = 0.65 V vs. NHE in H2O) produced the corresponding sulfoxide with complete oxygen incorporation from the oxidant. Since an ET mechanism must certainly hold in the reactions of 10 and 11, the oxygen incorporation experiments indicate that the intermediate radical cation, once formed, has to react with PFe(IV)=O (the reduced form of the iron-oxo complex which is formed by the ET step) in a fast oxygen rebound. Thus, an ET step followed by a fast oxygen rebound is also suggested for the other sulfides investigated in this work.

IMPORTANCE OF SINGLE ELECTRON-TRANSFER IN SINGLET OXYGEN REACTION IN AQUEOUS SOLUTION. OXIDATION OF ELECTRON-RICH THIOANISOLES

Oxidation of substituted thioanisoles by chemically generated singlet oxygen was investigated in polar aqueous media.The formation of the superoxide ion was observed during sulphoxidation of 4-hydroxythioanisole (4) in phosphate buffer at pH 7.5.Control e