36603-45-9

Usage

Physical form

White to off-white crystalline powder

Classification

Organic compound, sulfonylphenyl ketone

Main functional groups

Sulfonyl group, phenyl ring, ketone functional group

Uses

Building block in the synthesis of pharmaceutical and agrochemical compounds

Known properties

Anti-inflammatory, analgesic

Potential applications

Treatment of pain and inflammation-related conditions

Safety precautions

May be harmful if ingested or inhaled, can cause skin and eye irritation

Upstream product

• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 70-11-1 α-bromoacetophenone 
• 532-27-4 1-chloroacetophenone 
• 98-86-2 acetophenone 
• 1851-09-8 2-(4-chlorobenzenesulfonyl)acetonitrile 
• 100-03-8 4-chlorobenzenesulfinic acid 
• 536-74-3 phenylacetylene 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 100-42-5 styrene 
• 2751-25-9 p-chlorophenylsulfonyl hydrazide 
• 106-54-7 p-Chlorothiophenol 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 

Downstream Products

• 60416-89-9 (4-chloro-benzenesulfonyl)-methylsulfanyl-methane 
• 76283-85-7 2-(4-Chloro-benzenesulfonyl)-3-(1H-indol-3-yl)-1-phenyl-propan-1-one 
• 91781-50-9 α-<(p-chlorophenyl)sulfonyl>propiophenone 
• 64326-21-2 2-(4-chloro-benzenesulfonyl)-3-ethoxy-1-phenyl-propenone 
• 1104732-63-9 (E)-2-(4-chlorophenylsulfonyl)-1,5-diphenylpent-4-en-1-one 
• 61821-14-5 2-(4-Chloro-benzenesulfonyl)-2-ethoxy-1-phenyl-ethanone 
• 41997-88-0 2-(4-Chloro-benzenesulfonyl)-2-methoxy-1-phenyl-ethanone 
• 91781-47-4 p-chlorophenyl isopropenyl sulfone 
• 162777-25-5 Z-1,2-bis(4-chlorophenylsulfonyl)-1,2-bis(methylthio)-ethylene 

Relevant academic research and scientific papers

Method for preparing beta-carbonyl sulfone compound by using half-sandwich iridium complex

The invention relates to a method for preparing a beta-carbonyl sulfone compound by using a half-sandwich iridium complex, which comprises the following step: in the presence of alkali, by taking acetophenone and sulfonyl chloride as raw materials and taking the half-sandwich iridium complex containing an o-carboborylbenzoxazole structure as a catalyst, conducting reacting at room temperature to prepare the beta-carbonyl sulfone compound. Compared with the prior art, the method has the advantages that the half-sandwich iridium complex containing the o-carboborylbenzoxazole structure is used as the catalyst, acetophenone and sulfonyl chloride are efficiently catalyzed to react under the room temperature condition to synthesize the beta-carbonyl sulfone compound, the product yield is high, the reaction condition is mild, the substrate is cheap and easy to obtain, and the catalytic efficiency is high.

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.

Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis

A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.

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.

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.

A glucose oxidase-hemoglobin system for efficient oxysulfonylation of alkenes/alkynes in water

Background: β-ketosulfones are important bioactive compounds that have been extensively studied in organic chemistry. In this work, a green and efficient process for the synthesis of β-ketosulfones from alkenes (1) or alkynes (3) with sodium benzenesulfinate (2) was developed. Results: Under optimal conditions (alkenes (0.5 mmol) or alkynes (0.5 mmol), sodium benzenesulfinate (0.5 mmol), water (2 mL), hemoproteins (heme concentration: 0.06 mol%), GOX (42 U/ml), room temperature, 2 h), high yields of β-ketosulfones could be obtained when HgbRb (hemoglobin from rabbit blood) and GOX (glucose oxidase from Aspergillus niger) was used as the catalyst. Conclusion: This enzymatic method demonstrates the great potential for the synthesis of β-ketosulfones and extends the application of dual protein systems in organic synthesis.

A Compartmentalized-type Bifunctional Magnetic Catalyst for One-pot Aerobic Oxysulfonylation and Asymmetric Transfer Hydrogenation

Utilization of the confined cavity of the mesoporous silica, the exploration of the synergetic catalysis process for sequential organic transformations has great significance in asymmetric catalysis. In this study, the yolk-shell-structured magnetic nanoparticles with the chiral Ru/diamine species within the nanochannels of the outer mesoporous silica shell and the FeCl3 species on the inner magnet core are fabricated. The electron microscopy images and the structural characterizations disclose the uniformly distributed magnetic nanoparticles with the well-defined single-site ruthenium/diamine active centers onto the outer silica shell. As a yolk-shell-structured bifunctional magnet catalyst, the FeCl3 species enables an efficient aerobic oxysulfonylation between aryl-substituted terminal alkynes and sodium sulfinates to the β-keto sulfones intermediates, and the ruthenium/diamine species sequentially reduces the in-situ generated intermediate to the chiral β-hydroxysulfones products. As we envision, this one-pot aerobic oxysulfonylation/asymmetric transfer hydrogenation process affords various chiral β-hydroxysulfones in high yields with excellent enantioselectivities. Furthermore, this magnetic catalyst can also be conveniently recovered via an additional outer magnet and repeatedly recycled, showing a potential application in industrial interest.

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.

Dioxygen-Triggered Oxosulfonylation/Sulfonylation of Terminal Olefins toward β-Keto Sulfones/Sulfones

A dioxygen-triggered oxosulfonylation/sulfonylation of unactivated olefins to achieve β-keto sulfones/sulfones has been developed. Interestingly, pluralistic mechanisms were found when different types of compounds were applied as substrates, and different products were achieved. The reaction is carried out with a high atomic efficiency in the absence of a metal and a catalyst at room temperature under an air atmosphere. Importantly, as a proof-of-concept, a bioactive molecule was synthesized on a gram-scale level using this method.