65085-83-8

Usage

Uses

4-Acetyldiphenyl sulfone is used as an intermediate in organic synthesis.

InChI:InChI=1/C14H12O3S/c1-11(15)12-7-9-14(10-8-12)18(16,17)13-5-3-2-4-6-13/h2-10H,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 28525-13-5 4-(phenylsulfonyl)benzonitrile 
• 10169-55-8 1-[4-(phenylthio)phenyl]ethan-1-one 
• 873-55-2 sodium benzenesulfonate 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 515-42-4 sodium phenylsulfonate 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 13329-40-3 4-Iodoacetophenone 
• 99-90-1 para-bromoacetophenone 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 108-95-2 phenol 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 1788-10-9 4-Acetylbenzenesulfonyl chloride 
• 780-69-8 triethoxyphenylsilane 

Downstream Products

• 107920-73-0 N-(4-(phenylsulfonyl)phenyl)acetamide 
• 81830-82-2 α-methyl-α-furfuryl alcohol 
• 5361-54-6 4-(phenylsulfonyl)benzoic acid 

Relevant academic research and scientific papers

Microwaves assisted synthesis of antitumor agents of novel azoles, azines, and azoloazines pendant to phenyl sulfone moiety and molecular docking for VEGFR-2 kinase

The present research article contains two valuable starting phenylsulfone-enaminones which were synthesized in short reaction time with excellent yield under microwaves irradiation. These two enaminones were reacted with both nucleophiles and electrophiles to afford novel heterocycles bearing phenylsulfone moiety. The structure of all prepared phenylsulfone derivatives as well as their mechanistic pathways were studied based on their spectral data. Moreover, seventeen phenylsulfone derivatives were screened in vitro for their anticancer activity against HepG-2 and HCT-116 cell lines. Compounds 4 and 7a were equipotent to doxorubicin against HepG-2 cell line. Moreover, diphenyl sulfone derivative 7a was 3-fold more potent than doxorubicin against human colon cancer cell line with IC50 = 3.13 and 9.4 μg/mL, respectively. Remarkably, compound 7b was 2-fold more active than doxorubicin against the two tested cell lines. A docking study of title compounds into VEGFR-2 kinase was also conducted.

Pyridylidene Amide Ru Complex for Selective Oxidation in Organic Synthesis

The ruthenium(II) bis(PYA) complex 1 (PYA = p-pyridylidene amide) is a powerful catalyst for the oxidation of sulfides to sulfones, of alkenes to carbonyl compounds, and of terminal alkynes to carboxylic acids by using NaIO4 as the terminal oxidant. The catalytic system shows a broad functional group tolerance and rate differences between alkyne and sulfide oxidation that are sufficiently large to effectively achieve selective sulfide oxidation with exquisite selectivity.

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.

Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water

A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.

A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling

An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Method for synthesizing sulfone compounds under photocatalysis condition

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle

A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.

Hantzsch Ester as a Visible-Light Photoredox Catalyst for Transition-Metal-Free Coupling of Arylhalides and Arylsulfinates

Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (HEH) has been utilized as a visible-light photoredox catalyst for the cross coupling of arylhalides and arylsulfinates without transition metal, sacrificial agent, and mediator. This method is compatible with various functional groups and provides diaryl sulfones in good to high yields. Mechanistic studies indicate that this reaction undergoes the stepwise light irradiation of HE?, single electron transfer (SET) in donor–acceptor complex (DAC) from *HE? to arylhalide, trapping of aryl radical with sulfinate, and SET oxidation of sulfone radical anion by HE. to sulfone by the DAC method.

Method for preparing aryl sulfone compound as well as method for extracting catalyst and aryl sulfone compound

The invention provides a preparation method of an aryl sulfone compound, which is characterized in that in an organic solvent and under an aerobic atmosphere, a catalytic system composed of a metal-ligand-TEMPO is used for catalytic oxidation of a thioether compound to obtain the aryl sulfone compound. The preparation method is simple, green, and efficient, the reaction condition is mild, and theapplication range is wide; the invention also provides a method for extracting a catalyst and the product aryl sulfone compound used in the preparation process. The ethyl acetate is added to a reaction mixture, steps of filtering and condensation under reduced pressure are carried out to obtain a filtrate and the catalyst, and silica gel column chromatography and concentration extraction are carried out to obtain the aryl sulfone compound. The extraction method is simple, and the extracted catalyst has high activity and good cycle stability, and the extraction rate of the product aryl sulfonecompound is high.