87891-80-3

Upstream product

• 6388-72-3 2-(4-methoxyphenyl)oxirane 
• 873-55-2 sodium benzenesulfonate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 3959-23-7 benzenesulfonylacetic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 5535-48-8 PVS 
• 5720-07-0 4-methoxyphenylboronic acid 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 637-69-4 4-Methoxystyrene 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 98-09-9 benzenesulfonyl chloride 
• 768-60-5 4-methoxyphenylacetylen 

Downstream Products

• 1363721-82-7 (2R,3R)-3-fluoro-3-{2-[(S)-p-tolylsulfinyl]phenyl}-2-(4-methoxyphenyl)prop-1-yl phenyl sulfone 
• 1363721-92-9 (2S,3R)-3-fluoro-3-{2-[(S)-p-tolylsulfinyl]phenyl}-2-(4-methoxyphenyl)prop-1-yl phenyl sulfone 
• 104151-26-0 trans-1-methoxy-4-(2-cyclohexylethenyl)benzene 
• 1032938-02-5 (E)-2-(4-methoxystyryl)-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane 
• 1245924-48-4 1-((2S,3R)-3-(2-((S)-p-tolylsulfinyl)phenyl)-1-(phenylsulfonyl)butan-2-yl)-4-methoxybenzene 
• 934740-55-3 1-(4-methoxyphenyl)-2-(phenylsulfonyl)ethanol 
• 103786-20-5 (E)-1-methoxy-4-(3-methyl-but-1-en-1-yl)benzene 

Relevant academic research and scientific papers

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.).

Visible-Light-Induced Three-Component Intermolecular Trifluoromethyl-Alkenylation Reactions of Unactivated Alkenes

Herein, we describe a practical protocol for efficient, mild, visible-light-induced three-component intermolecular trifluoromethyl-alkenylation reactions of unactivated alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this protocol, we not only introduced a trifluoromethyl group into alkenes but also converted unactivated alkenes to styrene-based activated alkenes, in addition to accomplishing late-stage functionalization of pharmaceutical intermediates. (Figure presented.).

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

Visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones

Herein we report a mild, general protocol for visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones. The protocol permits efficient functionalization of sulfones with a broad range of cyclic and acyclic secondary and tert

PhB(OH)2-Promoted Electrochemical Sulfuration-Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation-Olefination

We report a PhB(OH)2-promoted electrochemical sulfuration-formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation-olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.

Vinyl sulfone synthesisviacopper-catalyzed three-component decarboxylative addition

The synthesis of vinyl sulfone derivativesviathe reaction of arylpropiolic acids, K2S2O5, and aryl boronic acids is reported. The CuBr2/1,10-phenanthroline catalytic system in the presence of acetic acid provide

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).

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.

Synthesis of vinyl sulfones through sulfonylation of styrenes with sulfonyl chlorides under metal-free conditions

A hypervalent iodine reagent-mediated sulfonylation of styrenes with sulfonyl chlorides was developed for the synthesis of vinyl sulfones. The reaction proceeded under metal-free, mild and neutral conditions without extra oxidants or bases. It also exhibited good air and moisture tolerance, broad substrate scope and high chemo-selectivity, affording the vinyl sulfones in moderate to good yields.