82652-18-4

Upstream product

• 67-71-0 dimethylsulfone 
• 26537-19-9 methyl 4-tert-butylbenzoate 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 1746-23-2 4-tert-Butylstyrene 
• 67-68-5 dimethyl sulfoxide 
• 772-38-3 4-tert-Butylphenylacetylene 

Downstream Products

• 1599463-34-9 (Z)-N-(1-(4-(tert-butyl)phenyl)-2-(methylsulfonyl)vinyl)acetamide 
• 110224-65-2 α-(4-tert-butylbenzyl)-β-anilinoacrylonitrile 
• 110224-66-3 2,4-diamino-5-(4-tert-butylbenzyl)pyrimidine 

Relevant academic research and scientific papers

Visible-light-promoted aerobic oxidative synthesis of β-ketosulfones under photocatalyst-free conditions

A simple and convenient visible-light-mediated method has been developed for the construction of β-ketosulfones via aerobic oxidative difunctionalization of alkynes with arylazo sulfones and dioxygen in air under photocatalyst-free conditions. The present photochemical methodology provides a facile and attractive protocol to construct a series of β-ketosulfones in moderate to good yields.

Preparation method of beta-carbonyl sulfone compound promoted by visible light

The invention discloses a preparation method of a beta-carbonyl sulfone compound promoted by visible light. The preparation method includes the following steps that olefin and aryl-sulphonazo are mixed with an organic solvent and water, and then a reaction is conducted for 16-24 hours at room temperature under visible illumination; and after the reaction, ethyl acetate is used for extracting reaction liquid, and the beta-carbonyl sulfone compound is obtained after concentration and column chromatography isolation of an extract. According to the method, clean light energy is used as reaction energy, oxygen in air is used as an oxidant and an oxygen source, the beta-carbonyl sulfone compound is effectively synthesized at the room temperature, the method does not require any photocatalyst orequivalent inorganic oxidant, and has the advantages of easy and convenient operation, low energy consumption, high reaction safety, environmental friendliness and the like.

Photocatalyst-Free Visible Light-Induced Synthesis of β-Oxo Sulfones via Oxysulfonylation of Alkenes with Arylazo Sulfones and Dioxygen in Air

A catalyst-free strategy has been established for the synthesis of β-oxo sulfones via visible light-induced oxysulfonylation of alkenes with arylazo sulfones with dioxygen in air. The present photoinduced transformation proceeds smoothly at room temperature in the absence of an external photosensitizer, which not only provides a mild and efficient approach to various β-oxo sulfones, but also opens a different reaction mode for the photochemical reaction of arylazo sulfones.

Nickel-Catalyzed Highly Enantioselective Hydrogenation of β-Acetylamino Vinylsulfones: Access to Chiral β-Amido Sulfones

The nickel/(S)-Binapine complex was found to be an efficient catalyst for asymmetric hydrogenation of β-acetylamino vinylsulfones to afford chiral β-Amido sulfones with excellent yields and enantioselectivities (up to 95% yields and >99% ee). This protocol has good compatibility with a series of substituted (Z)-β-acetylamino vinylsulfones or Z/E isomeric mixtures. A gram-scale reaction has also been achieved in the presence of a 0.2 mol % catalyst loading.

CO/O2 assisted oxidative carbon-carbon and carbon-heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins

Selective carbon-carbon and carbon-heteroatom bond cleavage was achieved in a one reaction system. With this strategy a novel Pd/Cu-catalyzed aerobic oxidative oxosulfonation of olefins with DMSO has been developed. Preliminary mechanistic investigations indicated that CO/O2 assisted the bond cleavage and the leaving groups from the starting materials were trapped by O2 and underwent a hydroxylation process.

Iron(III)-catalyzed aerobic oxidation and cleavage/formation of a C-S bond

A new iron(III)-catalyzed synthesis of β-oxo sulfones is described that employs vinylarenes and readily available dimethyl sulfoxide (DMSO) with hydrazine and oxygen as the oxidant. The reaction tolerates various functional group substituents on the vinylarene substrates to afford β-oxo sulfones in moderate to good yields. The cleavage and formation of the C-S bond are the key steps of this transformation.

Catalytic and direct methyl sulfonylation of alkenes and alkynes using a methyl sulfonyl radical generated from a DMSO, dioxygen and copper system

This paper describes an efficient method to β-keto methyl sulfones and (E)-vinyl methyl sulfones using DMSO as the substrate. The methyl sulfonyl radical generated from DMSO in the presence of catalytic Cu(i) under O2 atmosphere is believed to be involved in this reaction. Isotopic labeling and 18O2 experiments were performed to investigate the reaction mechanism.

2,4-Diamino-5-benzylpyrimidines as Antibacterial Agents. 8. The 3,4,5-Triethyl Isostere of Trimethoprim. A Study of Specificity

3,4,5-Triethylacetophenone was synthesized in 60percent yield by a Friedel-Crafts reaction from 4-ethylacetophenone and converted to 2,4-diamino-5-(3,4,5-triethylbenzyl)pyrimidine (2), a trimethoprim (1) isostere, by standard techniques.This compound is more lipophilic than 1 by three log units (log P, octanol/water).Compound 2 was approximately equipotent with 1 in inhibiting Escherichia coli dihydrofolate reductase (DHFR), 2-fold more potent against P. berghei and N. gonorrhoeae DHFR, and 10 and 25 times better an inhibitor of rat and chicken liver DHFR, respectively.Although the 3,4-dimethoxy analogue 19 was 10-fold less inhibitory to E. coli DHFR than 1, it was 3-4 times more potent on the vertebrate isozymes, whereas the diethyl congener 10 followed 19 in its E. coli DHFR binding but was less active on rat and chicken DHFR.Therefore, a significant portion of the selectivity of 1 for bacterial, as opposed to vertebrate, DHFR, involves the methoxy functions.An analysis of the X-ray data on 1 and 2 complexed with chicken DHFR, coupled with kinetic data, led to the conclusion that the differences in binding energies of the methoxy and ethyl compounds probably involve desolvation factors, as well as direct energies of interaction with protein atoms.Thus, one cannot invoke lipophilicity or shape alone in explaining the relationship in properties of 1 and 2.