27918-37-2

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 94-30-4 ethyl 4-methoxybenzoate 
• 637-69-4 4-Methoxystyrene 
• 80-17-1 benzenesufonyl hydrazide 
• 873-55-2 sodium benzenesulfonate 
• 108-98-5 thiophenol 
• 98-09-9 benzenesulfonyl chloride 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 768-60-5 4-methoxyphenylacetylen 
• 34910-42-4 1-(1-azidovinyl)-4-methoxybenzene 
• 6602-32-0 2-bromo-pyridin-3-ol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 4023-80-7 1-(4-methoxyphenyl)butan-1,3-dione 

Downstream Products

• 28322-57-8 4-methoxy-α-diazo-α-benzenesulfonyl acetophenone 
• 31663-21-5 2-Benzenesulfonyl-1-(4-methoxy-phenyl)-3-phenyl-propan-1-one 
• 31663-23-7 2-Benzenesulfonyl-1-(4-methoxy-phenyl)-butan-1-one 
• 31663-26-0 3-Benzenesulfonyl-4-(4-methoxy-phenyl)-4-oxo-butyric acid ethyl ester 
• 31663-22-6 2-Benzenesulfonyl-1-(4-methoxy-phenyl)-propan-1-one 
• 21160-15-6 Phenyl-<α-(4-methoxy-benzoyl)-α-methoxy-methyl>-sulfon 
• 61821-07-6 2-Benzenesulfonyl-2-ethoxy-1-(4-methoxy-phenyl)-ethanone 
• 1304145-17-2 (Z)-1-(4-methoxyphenyl)-4-phenylsulfonyl-3-(4-methylphenyl)-2-buten-1-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 60755-22-8 1-(4-methoxyphenyl)-4-phenyl-1,4-butanedione 
• 15982-64-6 1,4-bis(4-methoxyphenyl)butane-1,4-dione 
• 17171-17-4 4'-methoxy-3-methylbiphenyl 
• 22966-19-4 trans-4'-methoxychalcone 
• 7448-86-4 1-(4-methoxyphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Molecular iodine mediated oxidative coupling of enol acetates with sodium sulfinates leading to β-keto sulfones

An efficient, transition metal-free protocol for direct oxidative sulfonylation of enol acetates with readily available sodium sulfinates has been developed using molecular iodine as an oxidant. The reaction follows a free radical pathway and offers a more practical, economical, safer, and environmentally benign approach to a variety of β-keto sulfones in a one-pot procedure.

Synthesis of β-Keto Sulfones by Oxy-Sulfonylation of Alkynes in HFIP

Herein, we have established a method for the construction of β-keto sulfones through aerobic oxy-sulfonylation of alkynes with sulfinates. The reaction performed employing air as the oxidant and oxygen source. Moreover, this protocol exhibits low consume of sulfinates, short reaction period, and minimal waste. Mechanism study and density functional theory (DFT) calculation showed that the solvent played a significant role in the transformation. (Figure presented.).

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.

Chemoenzymatic Oxosulfonylation-Bioreduction Sequence for the Stereoselective Synthesis of β-Hydroxy Sulfones

A series of optically active β-hydroxy sulfones has been obtained through an oxosulfonylation-stereoselective reduction sequence in aqueous medium. Firstly, β-keto sulfones were synthesized from arylacetylenes and sodium sulfinates to subsequently develop the carbonyl reduction in a highly selective fashion using alcohol dehydrogenases as biocatalysts. Optimization of the chemical oxosulfonylation reaction was investigated, finding inexpensive iron(III) chloride hexahydrate (FeCl3 ? 6H2O) as the catalyst of choice. The selection of isopropanol in the alcohol-water media resulted in high compatibility with the enzymatic process for enzyme cofactor recycling purposes, providing a straightforward access to both (R)- and (S)-β-hydroxy sulfones. The practical usefulness of this transformation was illustrated by describing the synthesis of a chiral intermediate of Apremilast. Interestingly, the development of a chemoenzymatic cascade approach avoided the isolation of β-keto sulfone intermediates, which allowed the preparation of chiral β-hydroxy sulfones in high conversion values (83–94 %) and excellent optical purities (94 to >99 % ee).

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.

One-pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water

A novel, facile and efficient strategy for the one-pot synthesis of β-ketosulfones from readily available sulfonyl chloride, hydrazine hydrate and vinyl azides is described. The reaction proceeded very smoothly affording diverse β-ketosulfones in moderate to good yields. This new procedure has the advantages of environmental benign, easy and simple operation, low cost and wide tolerance of functional groups, which provides a highly fascinating protocol to access β-ketosulfones.

Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro

Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.

Pd-Catalyzed Annulation of β-Iodovinyl Sulfones with 2-Halophenols: A General Route for the Synthesis of 3-Sulfonyl Benzofuran Derivatives

The palladium-catalyzed annulation between β-iodovinyl sulfones and 2-halophenols or 1-bromo-2-naphthol or 2-bromo-3-pyridinol is presented. The annulation process involving oxa-Michael addition-elimination and intramolecular Heck reaction leading to form

Efficient synthesis of chiral β-hydroxy sulfones: Via iridium-catalyzed hydrogenation

A highly efficient Ir/f-Amphol-catalyzed asymmetric hydrogenation of prochiral β-keto sulfones was successfully developed to prepare a series of chiral β-hydroxy sulfones with good to excellent results (62%->99% conversions, 35%-99% yields and 86%->99% ee). Our Ir/f-Amphol L4 catalytic system exhibited very high activity; the gram-scale asymmetric hydrogenation was performed well with just 0.005 mol% catalyst loading (S/C = 20,000) to afford the desired product 2a with >99% conversion, 99% yield and 93% ee.