40807-08-7

Upstream product

• 2788-86-5 4-Chlorostyrene oxide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 4251-65-4 (4-chlorophenyl)acetaldehyde 
• 3937-96-0 tosylacetic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 5554-81-4 {[(4-methylphenyl)sulfonyl]methylidene}(triphenyl)-λ⁵-phosphane 
• 1615-02-7 p-chlorocinnamic acid 
• 1950-78-3 p-toluenesulfonyl iodide 
• 873-73-4 4-n-chlorophenylacetylene 
• 106-45-6 para-thiocresol 
• 657-84-1 sodium tosylate 
• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 

Downstream Products

• 86432-61-3 C₁₆H₁₅ClO₂S 
• 88017-66-7 trans epoxy-p-chlorostyryl p-tolylsulphone 
• 873-73-4 4-n-chlorophenylacetylene 
• 1620445-83-1 (E)-N-(3-(4-chlorophenyl)allyl)-N-methylacetamide 
• 1574116-76-9 1-benzyl-3-(4-chlorophenyl )-N-(2,2-dimethyl-propyl)-N-methyl-4-methylsulfonyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid amide 
• 1574112-38-1 [1-benzyl-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrol-2-yl]-(3,3-difluoro-azetidin-1-yl)-methanone 
• 1574113-06-6 1-benzyl-3-(4-chlorophenyl)-4-cyclopropyl-N-(2,2-dimethyl-propyl)-N-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid amide 

Relevant academic research and scientific papers

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.

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.

Electrochemical Synthesis of Vinyl Sulfones by Sulfonylation of Styrenes with a Catalytic Amount of Potassium Iodide

An electrochemical sulfonylation reaction of styrenes was developed in which sodium arylsulfinates were used as sulfonylating reagents, a catalytic amount of KI was used as a redox mediator, and Bu 4NBF 4was used as the electrolyte. In addition to various styrenes, sodium arylsulfinates with either electron-donating or electron-withdrawing groups were tolerated.

Cu-catalyzed dehydrogenative olefinsulfonation of Alkyl arenes

A copper-catalyzed reaction protocol for the dehydrogenation of ethylbenzenes into styrene derivatives has been developed. This reaction procedure proceeded well under mild reaction conditions, providing a practical and efficient strategy for the rapid assembly of biologically and pharmaceutically significant molecules, such as vinyl sulfone. Simple alkyl arenes were functionalized via consecutive β-elimination in the presence of N-sulfonylbenzo[d]imidazole with broad substrate scope and good functional group tolerance.

N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature

N,N′-Disulfonylhydrazines have been proven to be the most reactive precursors of sulfonyl radicals in all types of sulfonyl substituted hydrazines as early as a half century ago. But such function has not been applied in organic synthesis except the formation of disulfones by self-dimerization of sulfonyl radicals. In this article, they were introduced as new sulfonylating reagents and their combinations with NIS and Et3N were established as excellent iodosulfonylating reagents for alkenes. Finally, a highly efficient method for the synthesis of (E)-vinyl sulfones was developed by mixing an alkene, a N,N′-disulfonylhydrazine, NIS and Et3N in THF at room temperature for 5 min.

Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: A metal- And oxidant-free protocol for the synthesis of (: E)-vinyl sulfones in water

An efficient electrochemical transformation of a variety of alkenes and sulfonyl hydrazides into vinyl sulfones with a catalytic amount of tetrabutylammonium iodide in water is reported. The reaction proceeds smoothly to afford vinyl sulfones with good selectivities and yields at room temperature under air in an undivided cell. Cyclic voltammograms and control experiments have been performed to provide preliminary insight into the reaction mechanism. The key features of this reaction include using pure water as solvent, transition metal- and oxidant-free conditions, and being easily scaled up to gram-scale synthesis. This journal is

Copper(II) Acetate Mediated Synthesis of 3-Sulfonyl-2-aryl-2 H -chromenes

This paper describes a concise, easy-operation, high-yielding method for the synthesis of 3-sulfonyl-2-aryl-2 H -chromenes by a one-pot, straightforward two-step synthetic route, which includes (i) Cu(OAc) 2 /PyBOP-mediated intermolecular [4+2] annulation of substituted salicylic acids with β-sulfonylstyrenes in the presence of DMAP in refluxing DMF, and (ii) sequential O -alkylation of the resulting sulfonylflavanones with n -butyl bromide. A plausible mechanism is proposed and discussed. This protocol provides a highly effective annulation via one carbon-oxygen (C-O) and one carbon-carbon (C-C) bond formations.

Electron Donor-Acceptor Complex Enabled Decarboxylative Sulfonylation of Cinnamic Acids under Visible-Light Irradiation

Visible-light-induced decarboxylative sulfonylation of cinnamic acids with aryl sulfonate phenol esters enabled by the electron donor-acceptor complex is developed. The method offers a mild and green approach for the synthesis of vinyl sulfones with excellent functional group compatibility under photocatalyst and oxidant-free conditions.

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

E -Selective synthesis of vinyl sulfones via silver-catalyzed sulfonylation of styrenes

An efficient and highly E-selective protocol for the synthesis of vinyl sulfones is described. This simple protocol demonstrates the first synthesis of vinyl sulfones via a silver-catalyzed C-S bond coupling reaction. In addition, the success of the reaction was found to be critically dependent on the use of TEMPO as the additive.