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• 139-66-2 diphenyl sulfide 
• 945-51-7 1,1'-sulfinylbisbenzene 

Relevant academic research and scientific papers

Metal-Free Synthesis of Sulfones and Sulfoxides through Aldehyde-Promoted Aerobic Oxidation of Sulfides

Metal-free aerobic oxidation of aryl sulfides to sulfoxides and sulfones has been developed in the presence of aliphatic aldehydes with excellent selectivity and yields. The reaction proceeded under mild conditions with the catalysis of N-hydroxyphthalimide (NHPI). Control experiments indicated that the reaction underwent a free radical pathway with the acylperoxyl radicals generated from aldehydes in situ as the key intermediates. The aromatic aldehydes were less efficient in the sulfide oxidation, which might be explained by the fact that the aromatic ring dispersed the electrons of free radicals and thus weakened the attacking ability of peroxy free radicals. Graphic Abstract: [Figure not available: see fulltext.]

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

Integrating hydrogen production with anodic selective oxidation of sulfides over a CoFe layered double hydroxide electrode

Replacing the sluggish oxygen evolution reaction (OER) with oxidation reactions for the synthesis of complex pharmaceutical molecules coupled with enhanced hydrogen evolution reaction (HER) is highly attractive, but it is rarely explored. Here, we report an electrochemical protocol for selective oxidation of sulfides to sulfoxides over a CoFe layered double hydroxide (CoFe-LDH) anode in an aqueous-MeCN electrolyte, coupled with 2-fold promoted cathodic H2productivity. This protocol displays high activity (85-96% yields), catalyst stability (10 cycles), and generality (12 examples) in selective sulfide oxidation. We demonstrate its applicability in the synthesis of four important pharmaceutical related sulfoxide compounds with scalability (up to 1.79 g). X-ray spectroscopy investigations reveal that the CoFe-LDH material evolved into amorphous CoFe-oxyhydroxide under catalytic conditions. This work may pave the way towards sustainable organic synthesis of valuable pharmaceuticals coupled with H2production.

Electrochemical Scalable Sulfoxidation of Sulfides with Molecular Oxygen and Water

An efficient and chemoselective synthesis of sulfoxides through the electrooxidation of sulfides has been well developed. This protocol takes advantage of electricity as the terminal oxidant and of molecular oxygen and water as the oxygen atom sources. A variety of structurally diverse sulfoxide compounds are assembled in moderate to excellent yields. The scaled-up reactions at 6–20 mmol show the good practicability and application potential of this methodology. A possible free radical mechanism has been proposed to rationalize the reaction procedure.

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides

The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.

Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O2/Air

A practical and switchable method for the synthesis of aryl sulfones and sulfoxides via sulfide oxidation was developed. The chemoselectivities of products were simply controlled by reaction temperature using O2/air as the terminal oxidant and oxygen source. The broad substrate scope, easy realization of gram-scale production, and the simplification of a sulfide oxidation system render the strategy attractive and valuable.

Mechanistic studies on a sulfoxide transfer reaction mediated by diphenyl sulfoxide/triflic anhydride

Sulfoxides are frequently used in organic synthesis as chiral auxiliaries and reagents to mediate a wide variety of chemical transformations. For example, diphenyl sulfoxide and triflic anhydride can be used to activate a wide range of glycosyl donors inc

Dramatic Change of Carbonyl Oxide Reactivity by the Potent Electron-Withdrawing Trifluorompthyl Group

α,α,α-Trifluoroacetophenone oxide, generated by 1O2 oxidation of Ph(CF3)CN2, reacted electrophilically with sulfoxides (ρ = -0.74 vs σ r = 0.95) affording sulfides as the major product. The intermediacy of persulfoxides formed via cyclic peroxidic sulfuranes in the novel deoxygenation was evidenced by an 18O-tracer study and by the formation of benzaldehyde in the reaction with benzyl phenyl sulfoxide. Olefins were oxidized to epoxides during the photooxidation of Ph(CF3)CN2. From the fact that the epoxidation proceeded almost stereospecifically and the substituent effect on styrenes resulted in the negative ρ-value of -1.66 vs σ(r = 0.97), a dioxirane was proposed as the second intermediate which might be formed by the isomerization of carbonyl oxide. Trapping experiments with styrenes and sulfoxides suggested that the cyclization of carbonyl oxide is competitive with the reaction with sulfoxides. In contrast to the known nucleophilic nature of carbonyl oxides, the present oxide is shown to have an electrophilic character, indicating that the reactivity of carbonyl oxides could be controlled by substituants.

Reactivity of nitroso oxides: Effect of polar substituents and reaction mechanism

The structure and reactivity of nitroso oxide intermediates has been studied by trapping and tracer experiments in the photooxidation of substituted phenyl azides. O-Transfers with p-methoxyphenyl nitroso oxide were efficient and showed the reactivity order of PhN=O > Ph2S > Ph2SO > PhH. Sulfides and sulfoxides were oxidized electrophilically and the partial rate factor for the hydroxylation of benzenes afforded a negative ρ-value of -1.40 (σ+). In the case of the p-nitrophenyl isomer, the radical reactivity was much more significant as exemplified in the hydrogen abstraction from toluene. Both isomers behave as electrophilic radicals as shown by the relative rates of hydrogen abstraction from aliphatic C-H bonds, i.e., 1°:2°:3° = 1:7:50-60. An 18O-tracer study revealed that the intramolecular cyclization of aryl nitroso oxides is competitive with intermolecular O-transfers. Copyright 1996 by the Royal Society of Chemistry.