40949-56-2

Usage

Uses

Used in Pharmaceutical Industry:
[(4-Methylphenyl)sulfonyl]pyridinioamine anion is used as a synthetic intermediate for the development of bioactive molecules due to the presence of the sulfonyl group, which can be utilized in the synthesis of pharmaceutical compounds.
Used in Coordination Chemistry:
[(4-Methylphenyl)sulfonyl]pyridinioamine anion is used as a ligand in coordination chemistry, where the pyridinioamine moiety can form complexes with metal ions, potentially leading to new materials with unique properties.
Used in Organic Synthesis:
[(4-Methylphenyl)sulfonyl]pyridinioamine anion is used as a building block in the construction of complex organic compounds, where its unique chemical structure can be exploited to create novel molecules with specific functionalities.
Further research and exploration of the properties and reactivity of [(4-Methylphenyl)sulfonyl]pyridinioamine anion may reveal additional applications in the fields of chemical and pharmaceutical sciences.

InChI:InChI=1/C12H13N2O2S/c1-11-5-7-12(8-6-11)17(15,16)13-14-9-3-2-4-10-14/h2-10,13H,1H3/q+1

Upstream product

• 110-86-1 pyridine 
• 941-55-9 4-toluenesulfonyl azide 
• 75732-31-9 N-(p-methylbenzenesulfonyl)-N,O-bis(trimethylsilyl)hydroxylamine 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 98-59-9 p-toluenesulfonyl chloride 
• 39996-41-3 1-aminopyridinium mesitylenesulphonate 
• 6295-87-0 N-aminopyridin-1-ium iodide 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 

Downstream Products

• 1274906-16-9 N-(6-(tert-butyldimethylsilyloxy)-1-(2-oxooxazolidin-3-yl)hex-2-enylidene)-4-methylbenzenesulfonamide 
• 1385096-46-7 C₁₃H₁₁F₃N₂O₂S 
• 1385096-44-5 C₁₃H₁₃F₃N₂O₂S 
• 56983-95-0 2-phenylpyrazolo[1,5-a]pyridine 
• 158038-67-6 methyl 4-{[(4-methylphenyl)sulfonyl]amino}benzoate 

Relevant academic research and scientific papers

Visible-Light-Induced Remote C(sp3)-H Pyridylation of Sulfonamides and Carboxamides

Visible-light-induced site-selective C(sp3)-H pyridylation of amides has been accomplished using N-amidopyridinium salts. The N-centered radicals generated by the single-electron reduction of N-amidopyridinium substrates undergo 1,5-hydrogen at

Regiodivergent Conversion of Alkenes to Branched or Linear Alkylpyridines

Herein we report a practical protocol for the visible-light-induced regiodivergent radical hydropyridylation of unactivated alkenes using pyridinium salts. This approach provides a unified synthetic platform to control the regioselectivity of the synthesis of linear or branched C4-alkylated pyridines. A remarkable selectivity switch from the anti-Markovnikov to the Markovnikov product can be achieved by the addition of tetrabutylammonium bromide. The versatility of this protocol is further demonstrated based on the late-stage functionalization in pharmaceuticals.

Micellar Catalysis: Visible-Light Mediated Imidazo[1,2-a]pyridine C—H Amination with N-Aminopyridinium Salt Accelerated by Surfactant in Water

A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported, charactering mild and environmentally benign conditions, as well as great functional grou

Visible-Light-Induced ortho-Selective Migration on Pyridyl Ring: Trifluoromethylative Pyridylation of Unactivated Alkenes

The photocatalyzed ortho-selective migration on a pyridyl ring has been achieved for the site-selective trifluoromethylative pyridylation of unactivated alkenes. The overall process is initiated by the selective addition of a CF3 radical to the alkene to provide a nucleophilic alkyl radical intermediate, which enables an intramolecular endo addition exclusively to the ortho-position of the pyridinium salt. Both secondary and tertiary alkyl radicals are well-suited for addition to the C2-position of pyridinium salts to ultimately provide synthetically valuable C2-fluoroalkyl functionalized pyridines. Moreover, the method was successfully applied to the reaction with P-centered radicals. The utility of this transformation was further demonstrated by the late-stage functionalization of complex bioactive molecules.

Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides

By utilizing an underexplored reactivity mode of N-aminopyridinium ylides, we developed the visible-light-induced ortho-selective aminopyridylation of alkenes via radical-mediated 1,3-dipolar cycloaddition. The photocatalyzed single-electron oxidation of N-aminopyridinium ylides generates the corresponding radical cations that enable previously inaccessible 1,3-cycloaddition with a broader range of alkene substrates. The resulting cycloaddition adducts rapidly undergo subsequent homolytic cleavage of the N-N bond, conferring a substantial thermodynamic driving force to yield various β-aminoethylpyridines. Remarkably, amino and pyridyl groups can be installed into both activated and unactivated alkenes with modular control of ortho-selectivity and 1,2-syn-diastereoselectivity under metal-free and mild conditions. Combined experimental and computational studies are conducted to clarify the detailed reaction mechanism and the origins of site selectivity and diastereoselectivity.

Alkene functionalization for the stereospecific synthesis of substituted aziridines by visible-light photoredox catalysis

A novel strategy involving visible-light-induced functionalization of alkenes for the synthesis of substituted aziridines was developed. The readily prepared N-protected 1-aminopyridinium salts were used for the generation of N-centered radicals. This approach allowed the synthesis of aziridines bearing various functional groups with excellent diastereoselectivity under mild conditions. Moreover, this protocol was successfully applied to prepare structurally diverse nitrogen-containing frameworks.

Regiospecific Three-Component Aminofluorination of Olefins via Photoredox Catalysis

Direct visible-light-mediated aminofluorination of styrenes has been developed with high regioselectivity. Shelf-stable N-Ts-protected 1-aminopyridine salt was used as the nitrogen-radical precursor, and the commercially available hydrogen fluoride-pyridi

Visible-Light-Induced Aza-Pinacol Rearrangement: Ring Expansion of Alkylidenecyclopropanes

A novel visible-light-induced aza-pinacol rearrangement was developed for the first time. In this approach, the addition of the N-centered radical to the C=C bond of alkylidenecyclopropanes delivers a variety of cyclobutanimines and γ-butyrolactones, with

METHOD FOR PRODUCING COMPOUND HAVING 1,2-AMINO ALCOHOL SKELETON

PROBLEM TO BE SOLVED: To provide a method for producing 1,2-amino alcohols that has a high regioselectivity and is safe and efficient. SOLUTION: Provided is a method for producing 1,2-amino alcohols represented by formula 3 below by letting an electrophil

Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis

A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N-protected 1-aminopyridinium salts are the key compounds and serve as amidyl radical precursors by the action of Ir photocatalysts, fac-[Ir(ppy)3/s