4703-22-4

Usage

Chemical structure

Contains a piperidine ring with a sulfonyl group attached to a 4-methylphenyl moiety.

Usage

Commonly used as a precursor in the synthesis of various pharmaceuticals and agrochemicals.

Polar properties

The sulfonyl group imparts polar properties to the compound.

Acidic properties

The sulfonyl group also imparts acidic properties to the compound.

Basic properties

The presence of the piperidine ring confers basic properties to the compound.

Versatility

Useful in organic synthesis reactions and as a building block in the production of drugs and other bioactive compounds.

Applications

Finds applications in the pharmaceutical, chemical, and agricultural industries.

InChI:InChI=1/C12H17NO2S/c1-11-5-7-12(8-6-11)16(14,15)13-9-3-2-4-10-13/h5-8H,2-4,9-10H2,1H3

Upstream product

• 110-89-4 piperidine 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 29981-92-8 1-tosyl-3-methyl-imidazolium chloride 
• 92163-82-1 3-(p-tolylsulfonyl)-2(3H)-benzothiazolone 
• 16780-44-2 N-(5-hydroxy-pentyl)-4-methyl-benzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 155164-58-2 2-(4-methylbenzenesulfonyl)-4,5-dichloropyridazin-3-one 
• 1028-19-9 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole 
• 111-24-0 1,5-dibromo-pentane 
• 1136117-76-4 5-(4-methylphenylsulfonamido)pentyl 2-(hex-1-ynyl)-benzoate 
• 57392-61-7 toluene-4-sulfonic acid 2,2,2-trichloro-ethyl ester 
• 627-32-7 1-iodopropan-3-ol 
• 347885-68-1 4-bromo-1-tosylpiperidine 

Downstream Products

• 134415-28-4 1-<(4-Methylphenyl)sulfonyl>-2-methoxypiperidine 
• 91411-09-5 1-<(4-Methylphenyl)sulfonyl>-2,6-dimethoxypiperidine 
• 6091-44-7 piperidine hydrochloride 
• 1201516-76-8 2-(octan-2-yl)-1-tosylpiperidine 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 
• 63587-57-5 2-methyl-1-(toluene-4-sulfonyl)-piperidine 
• 1950-78-3 p-toluenesulfonyl iodide 
• 3333-08-2 N,N-dimethylpiperidinium iodide 

Relevant academic research and scientific papers

Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free

A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

S(vi) in three-component sulfonamide synthesis: Use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling

Sulfuric chloride is used as the source of the -SO2- group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki-Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved. This journal is

Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light

An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.

Synthesis method of aryl tertiary sulfonamide compounds promoted by visible light

The invention provides a synthesis method of aryl tertiary sulfonamide compounds promoted by visible light. In a non-protonic solvent, N-benzyl tertiary amine and arylsulfonyl chloride are used as rawmaterials, under the conditions of photosensitizer catalysis and illumination, a reaction is carried out for 1-4h at room temperature, and then separation and purification are carried out to obtain the product. The synthesis method of the aryl tertiary sulfonamide compound provided by the invention has the advantages of mild reaction conditions, simplicity and convenience in operation, short reaction time, no need of any transition metal catalysis and environmental friendliness.

A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes

We report herein a modular class of organic catalysts that, acting as donors, can readily form photoactive electron donor-acceptor (EDA) complexes with a variety of radical precursors. Excitation with visible light generates open-shell intermediates under mild conditions, including nonstabilized carbon radicals and nitrogen-centered radicals. The modular nature of the commercially available xanthogenate and dithiocarbamate anion organocatalysts offers a versatile EDA complex catalytic platform for developing mechanistically distinct radical reactions, encompassing redox-neutral and net-reductive processes. Mechanistic investigations, by means of quantum yield determination, established that a closed catalytic cycle is operational for all of the developed radical processes, highlighting the ability of the organic catalysts to turn over and iteratively drive every catalytic cycle. We also demonstrate how the catalysts' stability and the method's high functional group tolerance could be advantageous for the direct radical functionalization of abundant functional groups, including aliphatic carboxylic acids and amines, and for applications in the late-stage elaboration of biorelevant compounds and enantioselective radical catalysis.

Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2

Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds. Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate and the gradual release of alkyl iodide is crucial for the success of the reaction.

Red-light-mediated BartonMcCombie reaction

A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.

Method for hydrogenolysis of halides

The invention discloses a method for hydrogenolysis of halides. The invention discloses a preparation method of a compound represented by a formula I. The preparation method comprises the following step: in a polar aprotic solvent, zinc, H2O and a compound represented by a formula II are subjected to a reaction as shown in the specification, wherein X is halogen; Y is -CHRR or R; hydrogenin H2O exists in the form of natural abundance or non-natural abundance. According to the preparation method, halide hydrogenolysis can be simply, conveniently and efficiently achieved through a simple and mild reaction system, and good functional group compatibility and substrate universality are achieved.

Synthesis of sulfonamides promoted by alkyl iodide via a hypervalent iodine intermediate

A new method for the preparation of sulfonamides from sodium sulfinates and amines is developed. A stoichiometric amount of m-chloroperbenzoic acid as oxidant and a catalytic amount of 1-iodopropane provides the corresponding sulfonamides in good yields under mild reaction conditions. In this protocol, 1-iodopropane is first oxidized by m-chloroperbenzoic acid into the corresponding hypervalent iodine intermediate iodosylpropane, which is highly unstable and decomposes at once to form hypoiodous acid. Then, the following reaction of the generated active hypoiodous acid with sodium sulfinates and amines results in the corresponding sulfonamides.