61820-95-9

Usage

Uses

Used in Photopolymerization Processes:
4'-METHYL-2(P-TOLYL SULFONYL)ACETOPHENONE is used as a photoinitiator for initiating photopolymerization processes. It forms a stable free radical, which is crucial for the polymerization of certain materials under exposure to light, facilitating the curing of coatings, adhesives, and other polymeric systems.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 4'-METHYL-2(P-TOLYL SULFONYL)ACETOPHENONE is utilized as a key intermediate. Its role in the synthesis of various pharmaceutical compounds is significant, contributing to the development of new drugs and active pharmaceutical ingredients.
Used in Organic Material Synthesis:
4'-METHYL-2(P-TOLYL SULFONYL)ACETOPHENONE is also employed in the synthesis of other organic materials, where its reactivity and properties are leveraged to create a range of chemical products, from specialty chemicals to advanced materials for various applications.

InChI:InChI=1/C16H16O3S/c1-12-3-7-14(8-4-12)16(17)11-20(18,19)15-9-5-13(2)6-10-15/h3-10H,11H2,1-2H3

Upstream product

• 61737-10-8 1-(p-tolyl)-2-(p-tolylthio)ethan-1-one 
• 54731-27-0 1-p-methylphenyl-1-trimethylsiloxyethene 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 122-00-9 para-methylacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 766-97-2 4-n-methylphenylacetylene 
• 1338239-09-0 1-butyl-3-methylimidazolium p-toluenesulfinate 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 96475-75-1 4‐methylacetophenone oxime acetate 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 106-45-6 para-thiocresol 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 177750-08-2 1-(4-methylphenyl)ethenylacetamide 

Downstream Products

• 122772-73-0 (E)-1-Phenyl-3-pyridin-4-yl-2-(toluene-4-sulfonyl)-propenone 
• 122772-77-4 (E)-3-Pyridin-4-yl-2-(toluene-4-sulfonyl)-1-p-tolyl-propenone 
• 122772-78-5 (Z)-3-Thiophen-2-yl-2-(toluene-4-sulfonyl)-1-p-tolyl-propenone 
• 122772-75-2 (E)-3-(2-Hydroxy-phenyl)-2-(toluene-4-sulfonyl)-1-p-tolyl-propenone 
• 7383-90-6 3,4'-dimethylbiphenyl 
• 17286-62-3 2-(4-methylphenyl)quinoxaline 

Relevant academic research and scientific papers

Oxy-sulfonylation of terminal alkynesviaC-S coupling enabled by copper photoredox catalysis

We report the first literature example using visible light-induced trimethylsilyl azide (TMS-N3)-assisted copper-catalyzed oxy-sulfonylation of terminal C-C bonds to form β-keto sulfones (C-S bond formation). TMS-N3promotes the reaction by facilitating the formation of sulfonyl radicals, which later decompose into N2gas upon light irradiation. This method involves the use of commercially available and stable starting materials. Also, a wide range of functional groups have been well-tolerated under the current photoredox process, evading the side product formation. Potent biologically active compounds, such as CES1, 11β-HSD1 inhibitors, anti-analgesic agents, and reactive synthesis intermediates were synthesized to demonstrate the synthetic utility of the current methodology. Moreover, green chemistry metrics and Eco-scale evaluation for the current photochemical method show that the protocol is eco-friendly and highly efficient.

Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones

A copper-catalyzed aerobic oxidative cross-coupling reactions for the synthesis of β-ketosulfones via formation of a C[sbnd]S bond has been demonstrated. Promoted by the crucial copper catalyst, perfect selectivity and good to excellent yields could be achieved. This method, including inexpensive copper catalyst, wide functional group tolerance, and open air conditions, make it very attractive and practical. More importantly, it also provides a versatile tool for the construction of β-ketosulfones from basic starting materials under mild conditions.

Photosensitizer-free synthesis of β-keto sulfones: Via visible-light-induced oxysulfonylation of alkenes with sulfonic acids

A practical and environment-friendly methodology for the construction of β-keto sulfones through visible-light induced direct oxysulfonylation of alkenes with sulfonic acids at ambient temperature under open-air conditions was developed. Most importantly, the reaction proceeded smoothly without the addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste.

Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation

Charge separation plays a crucial role in regulating photochemical properties and therefore warrants consideration in designing photocatalysts. Metal–organic frameworks (MOFs) are emerging as promising candidates for heterogeneous photocatalysis due to their structural designability and tunability of photon absorption. Herein, we report the design of a pyrazole–benzothiadiazole–pyrazole organic molecule bearing a donor–acceptor–donor conjugated π-system for fast charge separation. Further attempts to integrate such a photosensitizer into MOFs afford a more effective heterogeneous photocatalyst (JNU-204). Under visible-light irradiation, three aerobic oxidation reactions involving different oxygenation pathways were achieved on JNU-204. Recycling experiments were conducted to demonstrate the stability and reusability of JNU-204 as a robust heterogeneous photocatalyst. Furthermore, we illustrate its applications in the facile synthesis of pyrrolo[2,1-a]isoquinoline-containing heterocycles, core skeletons of a family of marine natural products. JNU-204 is an exemplary MOF platform with good photon absorption, suitable band gap, fast charge separation, and extraordinary chemical stability for proceeding with aerobic oxidation reactions under visible-light irradiation.

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Cu(OTf)2-Catalyzed efficient sulfonylation of vinyl azides with sodium sulfinates

A simple oxidative cross-coupling reaction between vinyl azides and sodium sulfinates was developed. This reaction uses commercial arylsulfinates that are more efficient, cheaper, and more stable as sulfonylation reagents, for efficiently, cheaply, and environmentally friendly synthesis of β-keto sulfones. And the reaction has the advantages of simple operation, high efficiency, good yield, and also has a wide range of functional group tolerance.

Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides

Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.

Electrochemical Synthesis of β-Ketosulfones from Switchable Starting Materials

A synthesis of β-ketosulfones via sulfination of aryl methyl ketones and aryl acetylenes with sodium sulfinates under mild electrochemical conditions, in moderate to good chemical yields, is described. In particular, an electrochemical sulfination reaction of alkynes with sulfinate salts has never been explored. An environmentally friendly characteristic of this reaction is that it uses electricity as a valuable energy source for electrochemical synthesis of β-ketosulfones. This strategy is more convenient and practical compared to previous approaches.

Preparation method of beta-carbonyl sulfone compound

The invention discloses a preparation method of a beta-carbonyl sulfone compound, and belongs to the technical field of organic synthesis. The preparation method of the beta-carbonyl sulfone compoundis provided for solving the problems that in the prior art, operation is complex, the substrate range is narrow, and the functional group tolerance is poor. The preparation method comprises the stepsof taking a compound shown in formula I and a compound shown in formula II as raw materials, taking copper salt as a catalyst, carrying out reaction in an organic solvent, and after the reaction is completed, carrying out aftertreatment to obtain the beta-carbonyl sulfone compound. The preparation method is simple and convenient to operate, mild in reaction condition, wide in substrate range and good in functional group tolerance, the yield reaches up to 93%, and the synthesis cost is remarkably reduced.

Biomimetic photocatalytic sulfonation of alkenes to access β-ketosulfones with single-atom iron site

Biomimetic photocatalysis as an important organic transformation strategy has received increasing attention, with the performances of biomimetic catalysts largely depending on their design. This protocol has been initially used to fabricate a biomimetic photocatalyst of single-atom iron site through coupling carbon nitride with hemin (CNH) for the visible light-promoted sulfonation of alkenes to produce β-ketosulfones with up to 94% yield. The experimental results show that the role of CN in CNH is concentrated on enhancing the separation ability of photogenerated electron pairs and holes to improve the photocatalytic activity and stability. Moreover, the as-prepared photocatalyst of single atom iron can be irradiated under near-infrared light with a satisfactory yield, and is also feasible for the sulfonation reactions of androstenones. Importantly, this biomimetic catalysis-based synthesis system has some merits, namely high catalysis efficiency, favorable recyclability, high turnover number, and excellent functional group tolerance, making it promising for extensive applications in organic transformations for the synthesis of β-ketosulfones to access various bioactive drugs.