16212-08-1

Usage

Synthesis Reference(s)

Chemistry Letters, 15, p. 289, 1986Journal of the American Chemical Society, 102, p. 7603, 1980 DOI: 10.1021/ja00545a054The Journal of Organic Chemistry, 45, p. 406, 1980 DOI: 10.1021/jo01291a006

InChI:InChI=1/C15H14O2S/c1-13-7-9-15(10-8-13)18(16,17)12-11-14-5-3-2-4-6-14/h2-12H,1H3/b12-11+

Upstream product

• 17336-69-5 ω-p-Toluolsulfonyl-acetophenon-p-toluolsulfonylhydrazon 
• 3937-96-0 tosylacetic acid 
• 100-52-7 benzaldehyde 
• 37611-16-8 (E/Z)-styryl 4-methylbenzensulfonate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 774-48-1 (diethoxymethyl)benzene 
• 70-55-3 toluene-4-sulfonamide 
• 106-45-6 para-thiocresol 
• 96-09-3 styrene oxide 
• 42330-51-8 rac-(R)-1-phenyl-2-(p-tolylthio)ethan-1-ol 
• 71899-75-7 2-hydroxy-2-phenylethyl 4-methylphenyl sulfone 
• 4363-35-3 Dihydroxy-styryl-boran 
• 98-59-9 p-toluenesulfonyl chloride 
• 100-42-5 styrene 

Downstream Products

• 204389-35-5 (E)-4-methylphenyl 1-deuterio-2-phenylethenyl sulfone 
• 1239456-71-3 (E)-N-(2-methyl-1,3-diphenylprop-2-enyl)-4-methylphenylsulfonamide 
• 70197-09-0 N-(1-phenylpropyl)-4-toluenesulfonamide 
• 4874-85-5 1,5-diphenyl-1H-1,2,3-triazole 
• 19719-87-0 1-methyl-4-(phenethylsulfonyl)benzene 

Relevant academic research and scientific papers

PHOTODECOMPOSITION OF SELENOSULFONATES AND THEIR FACILE PHOTOADDITION TO ALKENES1

Phenyl areneselenosulfonates (1) are very photosensitive and easily undergo photodecomposition via initial homolysis of the Se-S bond.In the presence alkenes this facile photodissociation of 1 can be used to initiate a free radical chain reaction (eq 6) that leads to addition of 1 to the alkene to form β-phenylselenosulfones (2).The photoaddition requires much shorter reaction times than the non-photolytic addition of 1 to alkenes described recently.

Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature

Herein, metal-free radical Heck-type reaction of styrenes with sulfonyl hydrazides to synthesize vinyl sulfones is developed. The reaction is performed under economical TBAI/TBHP system on water in open air at room temperature, which proceeds through the

Alkyne-based, highly stereo- and regioselective synthesis of stereodefined functionalized vinyl tellurides

(Z)-β-Aryltellurovinylphosphonates and (Z)-β-aryltellurovinyl sulfones were synthesized via the highly stereoselective anti-hydrotelluration of 1-alkynylphosphonates and 1-alkynyl sulfones. The configurations of these compounds were characterized via sup

Photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls: Facile access to substituted dihydropyrazoles

A mild and efficient method for the photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls has been described. This strategy provides a potential protocol for the construction of functionalized 4,5-dihydropyrazoles in moderate to high yields.

One-pot approach for the regioselective synthesis of β-keto sulfones based on acid-catalyzed reaction of sulfonyl chlorides with arylacetylenes and water

Reaction of sulfonyl chlorides with arylacetylenes and water in the presence of a catalytic amount of sulfonic acid in THF provided β-keto sulfones in good yields with excellent regioselectivity.

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

The Sulfinylsulfonation of alkynes for β-Sulfinyl alkenylsulfone

Here we report the sulfinylsulfonation of alkynes to afford β-sulfinyl alkenylsulfone products with a broad substrate scope, excellent functional group compatibility, and high yield. Moreover, the sulfinylsulfonation reaction of enyne can also be realized for constructing functionalized carbo- and heterocycles through a radical cascade cyclization process.

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.

Copper-Catalyzed Heck-Type Couplings of Sulfonyl Chlorides with Olefins: Efficient and Rapid Access to Vinyl Sulfones

A copper-catalyzed redox-neutral alkene sulfonylation reaction has been developed. This reported protocol can be easily scale up to a gram scale, and smoothly applied to the late-stage modification of several bioactive molecules.

Generation of potent Nrf2 activators via tuning the electrophilicity and steric hindrance of vinyl sulfones for neuroprotection

Oxidative stress is constantly involved in the etiopathogenesis of an ever-widening range of neurodegenerative diseases. As a consequence, effective repression of cellular oxidative stress to a redox homeostatic condition is a promising and feasible strategy to treat, or at least retard the progression of, such disorders. Nrf2, a primary orchestrator of cellular antioxidant response machine, is responsible for detoxifying and compensating for deleterious oxidative stress via transcriptional activation of a diverse array of antioxidant biomolecules. In the framework of our persistent interest in disclosing small molecules that interfere with cellular redox-regulating machinery, we report herein the synthesis, optimization, and biological assessment of 47 vinyl sulfone scaffold-bearing small molecules, most of which exhibit robust neuroprotective effect against H2O2-mediated lesions to PC12 cells. After initial screening, the most potent neuroprotective compounds 9b and 9c with marginal cytotoxicity were selected for the follow-up studies. Our results demonstrate that their neuroprotective effects are attributed to the up-regulation of a panel of antioxidant genes and corresponding gene products. Further mechanistic studies indicate that Nrf2 is indispensable for the cellular performances of 9b and 9c, arising from the fact that silence of Nrf2 gene drastically nullifies their protective action. Taken together, 9b and 9c discovered in this work merit further development as neuroprotective candidates for the treatment of oxidative stress-mediated pathological conditions.