3406-03-9

Usage

Chemical Properties

light yellow crystalline powder

InChI:InChI=1/C14H12O3S/c15-14(12-7-3-1-4-8-12)11-18(16,17)13-9-5-2-6-10-13/h1-10H,11H2

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 93-89-0 benzoic acid ethyl ester 
• 51755-92-1 β-phenyl-β-hydroxyethyl phenyl sulfone 
• 873-55-2 sodium benzenesulfonate 
• 532-27-4 1-chloroacetophenone 
• 618-34-8 1-chlorostyrene 
• 100-34-5 benzene diazonium chloride 
• 98-81-7 1-bromovinylbenzene 
• 82211-05-0 1-phenyl-2-(phenylsulfonyl)-2-(phenylthio)ethan-1-one 
• 98-88-4 benzoyl chloride 
• 1666-13-3 diphenyl diselenide 
• 23128-59-8 ω-bromo-ω-phenylsulfonylacetophenone 
• 65-85-0 benzoic acid 
• 100-42-5 styrene 

Downstream Products

• 120219-69-4 α-phenylsulfonyl (3,4-dioxymethylene chalcone) 
• 51755-92-1 β-phenyl-β-hydroxyethyl phenyl sulfone 
• 38010-31-0 benzenesulfonyl-acetic acid anilide 
• 120219-68-3 α-benzenesulfonyl-4-methyl-cis-chalcone 
• 19232-53-2 (E)-1,3-diphenyl-2-(phenylsulfonyl)prop-2-en-1-one 
• 34545-07-8 2-phenyl-3-(phenylsulfonyl)quinoline 
• 29943-18-8 2-Benzenesulfonyl-5-ethylsulfanyl-1-phenyl-pentan-1-one 
• 61053-53-0 2-benzenesulfonyl-2-methanesulfonyl-1-phenylethanone 
• 122772-63-8 (E)-2-Benzenesulfonyl-1-phenyl-3-pyridin-2-yl-propenone 
• 122772-61-6 (E)-2-Benzenesulfonyl-1-phenyl-3-pyridin-3-yl-propenone 
• 122772-62-7 (Z)-2-Benzenesulfonyl-1-phenyl-3-thiophen-2-yl-propenone 
• 73779-25-6 2-(2-Benzenesulfonyl-ethyl)-4-chloro-phenol 
• 73779-24-5 1-(2-Benzenesulfonyl-ethyl)-naphthalen-2-ol 
• 59431-14-0 (methylsulfanyl)methyl phenyl sulfone 

Relevant academic research and scientific papers

Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation

Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.

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.

A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles

3-Fluoro- and trifluoromethylthio-piperidines represent important building blocks for discovery chemistry. We report a simple and efficient method to access analogs of these compounds that are armed with rich functionality allowing them to be chemoselectively derivatized with high diastereocontrol.

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.

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.

Method for synthesizing beta-ketosulfone derivative under mild condition and obtained beta-ketosulfone derivative

The invention discloses a method for synthesizing a beta-ketosulfone derivative under a mild condition, which comprises the following steps: dissolving aryl olefin and sodium sulfinate in a solvent in a reaction container, adding an acidic additive, sealing the reaction container under the conditions that air exists in the reaction container and no transition metal exists, and purifying after reaction to obtain the beta-ketosulfone derivative. The free radical addition oxidation reaction of olefin and sulfinic acid can be realized under the mild condition without transition metal, the reaction raw materials are cheap and easy to obtain, no organic metal reagent or transition metal is needed, air is used as an oxidizing agent, no dangerous peroxide or persulfide is needed, and the method is compatible with air. The method has the advantages of simple operation and the like, and overcomes the defects of transition metal participation, large catalyst consumption, expensive reagents, high method cost, more reaction steps, more by-products and the like in the prior art.

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.

Electrochemically Mediated Direct C(sp3)?H Sulfonylation of Xanthene Derivatives

The construction of C(sp3)-sulfonyl bonds through direct sulfonylation of C(sp3)?H bond presents a number of challenges, so an electrochemical oxidation-induced direct sulfonylation of the xanthene C(sp3)?H bond was developed. Significant advantages of this method are high atom efficiency, functional group tolerance, transition metal- and oxidant-free conditions. The in vitro cytotoxicity of all product is evaluated by MTT assay against human cancer cell lines. The results reveal that most of the compounds 3 da and 3 af have good inhibitory activity on tumor cell lines. (Figure presented.).

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 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.