58680-51-6

Upstream product

• 33533-58-3 phthalic acid mono-(4-methoxy-benzyl ester) 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 61885-76-5 E-p-Methoxyphenyl-p-tolylsulfinylsulfin 
• 270921-39-6 (4-methoxyphenyl)methyl methyl carbonate 
• 5023-68-7 4-methoxybenzyl-(4'-methylphenyl)-sulfide 
• 180746-15-0 1-methoxy-4-[(p-tolylsulfinyl)methyl]benzene 
• 61885-75-4 (E)-4-methoxy-S-oxo-Sλ⁴-dithiobenzoic acid S'-p-tolyl ester 
• 171628-53-8 N'-(4-methoxybenzylidene)methanesulfonohydrazide 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 123-11-5 4-methoxy-benzaldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 126616-34-0 5-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-3-methyl-1-(toluene-4-sulfonyl)-pentan-2-one 
• 126644-63-1 2',3'-isopropylidene-5'-(1-p-anisoyl-1-(tolylsulfonyl)-2-oxo-5-((tert-butyldiphenylsilyl)oxy)pent-3-yl)-5'-deoxyadenosine 
• 77853-42-0 4-(4-Methoxy-phenyl)-4-(toluene-4-sulfonyl)-butyronitrile 
• 72818-16-7 C₁₇H₁₈O₄S 
• 72457-25-1 4-(4-methoxyphenyl)butanenitrile 
• 126616-42-0 tert-Butyl-[5-(4-methoxy-phenyl)-3-methyl-pent-4-ynyloxy]-diphenyl-silane 
• 126616-38-4 C₄₈H₅₁O₈PSSi 
• 126616-40-8 2',3'-isopropylidene-5'-(1-p-anisoyl-1-(tolylsulfonyl)-2-((diphenoxyphosphinyl)oxy)-5-((tert-butyldiphenylsilyl)oxy)-2-penten-3-yl)-5'-deoxyadenosine 
• 72818-30-5 Anisoyl-4-tolylsulfon 

Relevant academic research and scientific papers

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.

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.

Synthesis of sulfone derivatives via palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides

A palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides for the synthesis of various benzyl sulfones is reported. This novel protocol shows widespread functional group tolerance, leading to the desired sulfones in moderate to excellent yields.

A general and practical sulfonylation of benzylic ammonium salts with sulfonyl hydrazides for the synthesis of sulfones

A practical and efficient approach adopting transition-metal-free cross-coupling of sulfonyl hydrazides with benzyl ammonium salts has been developed to synthesize benzyl sulfones using Cs2CO3 as base under mild conditions. The protocol employs stable and easy to handle coupling partners, and is endowed with good substrate compatibility, leading to functional benzyl sulfones in good yields.

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.

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

Palladium Catalyzed Monoselective α-Arylation of Sulfones and Sulfonamides with 2,2,6,6-Tetramethylpiperidine·ZnCl·LiCl Base and Aryl Bromides

A palladium catalyzed Negishi-type α-arylation of sulfones and sulfonamides with a broad range of aryl bromides has been developed. The substrates are selectively metalated in situ with tmp·ZnCl·LiCl base (tmp: 2,2,6,6-tetramethylpiperidine) and cross-coupled in the presence of a catalyst system that is generated from Pd(dba)2 and XPhos. Electron-deficient, electron-rich, and heterocyclic aryl bromides have been successfully cross-coupled, and sensitive functional groups are well tolerated. Simple aryl bromides are converted overnight at 60 °C in THF while heteroaryl bromides are efficiently coupled within 2 h at 130 °C in a microwave reactor. The desired monoarylated α-branched benzyl sulfones and sulfonamides were obtained in good yields, and overarylation was not detected. The procedure is ideal for late stage functionalization in parallel medicinal chemistry.

One-pot synthesis of multifunctionalized cyclopropanes

A facile one-step synthetic protocol toward multifunctionalized cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a [2C+1C] annulation.

Synthesis of sulfones by iron-catalyzed decomposition of sulfonylhydrazones

The Fe-catalyzed decomposition of sulfonylhydrazones gives rise to sulfones. The reaction is quite general and allows the preparation of sulfones from a variety of aryl, alkyl, and α,β-unsaturated aldehydes and ketones. Crossover experiments reveal that the reaction is an intermolecular process, which may proceed by nucleophilic attack of the sulfinate anion on an iron carbene complex. Carbonyl compounds can be easily transformed into sulfones by Fe-catalyzed decomposition of the corresponding sulfonylhydrazones. The process most likely proceeds through an iron carbene complex and opens the door for the design of othernovel Fe-catalyzed reductive couplings. Copyright