24422-77-3

Upstream product

• 19737-99-6 (Z)-1-((2-chloro-1-phenylvinyl)sulfonyl)-4-methylbenzene 
• 672-65-1 (1-chloroethyl)benzene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-86-2 acetophenone 
• 23730-30-5 (Ξ)-toluene-sulfinic acid-(4)-((R)-1-phenyl-ethyl ester) 
• 64-18-6 formic acid 
• 98-85-1 1-Phenylethanol 
• 5395-20-0 1-methyl-4-(benzylsulfonyl)benzene 
• 616-38-6 carbonic acid dimethyl ester 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 60565-67-5 acetophenone (p-tolylsulfonyl)hydrazine 
• 26958-46-3 1-(2,2-Bis-methylsulfanyl-1-phenyl-ethenesulfonyl)-4-methyl-benzene 
• 19737-98-5 (E)-aM-β-Chloro-α-p-tolylsulphonylstyrene 
• 23730-30-5 (Ξ)-toluene-sulfinic acid-(4)-((S)-1-phenyl-ethyl ester) 

Downstream Products

• 71376-57-3 p-tolyl 2-phenyl-2-propyl sulfone 
• 98-83-9 isopropenylbenzene 
• 71376-58-4 1-(1,2-Diphenyl-propane-2-sulfonyl)-4-methyl-benzene 

Relevant academic research and scientific papers

Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones

A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.

Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides

We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.

Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates

A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).

Method for alpha-position methylation of aryl benzyl sulfone compound

The invention discloses a method for alpha-position methylation of an aryl benzyl sulfone compound. The method comprises the following steps: sequentially adding the aryl benzyl sulfone compound, methanol, a metal precursor M, a ligand L, an alkaline substance and a solvent into a reactor, carrying out heating to 110-150 DEG C under the protection of nitrogen, conducting reacting for 20-30 hours,performing cooling to room temperature, conducting concentrating under reduced pressure, recovering the solvent and redundant methanol, and carrying out column chromatographic separation on residues to obtain the alpha-methylated aryl sulfone compound as shown in a formula (I). The method provided by the invention has the characteristics of easily available raw materials, simple operation, high chemical selectivity and regioselectivity and the like, meets the requirements of green chemistry, and has great implementation value and social and economic benefits.

Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism

Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.

Copper-Catalyzed Stereospecific C-S Coupling Reaction of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Methyl Triflate

A one-pot protocol for the synthesis of highly enantiopure benzylic thioethers, thioacetates, and sulfones (94-99% ee) via a ligand-free, copper-catalyzed stereospecific C-S coupling reaction of thiols and enantioenriched tertiary benzylic amines via in situ activation by methyl triflate is developed. Various enantioenriched tertiary benzylic amines, including 1-arylalkylamines, 1-tetrahydronaphthylethylamine, heterocyclic amines (e.g., 1-(thiophen-2-yl)ethanamine), and amino acid esters containing a benzylamine moiety, are highly efficient substrates, and their chirality is efficiently transferred to the products (94-99% ee). The absolute configurations of the products are predictable and follow the pattern of SN2-type substitutions; an inversion of the absolute configuration of the tertiary amines occurs during the C-S coupling reaction. Not only are various alkene-, arene-, and heteroarenethiols suitable for this C-S coupling reaction but also potassium thioacetate and sodium phenylsulfinate are as well. A plausible mechanism was proposed on the basis of the experimental results.

Stereospecific Nucleophilic Substitution of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Benzyne

A one-pot protocol has been developed for sequential benzyne activation and nucleophilic substitution of enantioenriched tertiary benzylic amines. In the presence of 2-(trimethylsilyl)phenyl triflate and CsF, a range of enantioenriched tertiary benzylic amines were substituted by various nucleophiles, delivering structurally diverse benzylic compounds in moderate to excellent yields with excellent retention of enantiopurity. Importantly, this operationally simple protocol permitted formation of various chiral C-S, C-Se, C-C, and C-N bonds with excellent enantiopurity under metal-free conditions.

Rh-Catalyzed Asymmetric Hydrogenation of α-Substituted Vinyl Sulfones: An Efficient Approach to Chiral Sulfones

Rh/(S)-(+)-DTBM-Segphos complex catalyzed asymmetric hydrogenation of α-substituted vinyl sulfones has been achieved, furnishing the desired products in high yields and excellent enantioselectivities (>90% yield, up to 99% ee). This method provided an eff

Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF3 · Et2O: Facile access to sulfinates and sulfones

An efficient BF3 · Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C–O and C–S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that provide highly stabilized carbocation in the reaction medium afforded sulfones as sole products. This study was aimed at understanding the regioselectivity of ambidentate sulfinate ion and to elucidate the interpretation of sulfinate/sulfone scaffolds.

Iron(III) phthalocyanine-chloride-catalyzed synthesis of sulfones from sulfonylhydrazones

In this study, sulfones are synthesized from sulfonylhydrazones catalyzed by iron(III) phthalocyanine chloride. This reaction offers broad substrate scope, occurs under mild conditions, utilized readily available reactants, and forms products in good-to-h