3237-31-8

Usage

InChI:InChI=1/C12H17NO2S/c14-16(15,12-9-5-2-6-10-12)13-11-7-3-1-4-8-11/h2,5-6,9-11,13H,1,3-4,7-8H2

Upstream product

• 108-91-8 cyclohexylamine 
• 98-09-9 benzenesulfonyl chloride 
• 155164-57-1 2-benzenesulfonyl-4,5-dichloropyridazin-3-one 
• 98-10-2 benzenesulfonamide 
• 110-83-8 cyclohexene 
• 98-11-3 benzenesulfonic acid 
• 35810-04-9 benzenesulfinic acid cyclohexylamide 
• 54769-59-4 N-hydroxybenzotriazole ester of benzenesulfonic acid 
• 108-94-1 cyclohexanone 
• 873-55-2 sodium benzenesulfonate 
• 110-82-7 cyclohexane 
• 80-17-1 benzenesufonyl hydrazide 
• 108-98-5 thiophenol 
• 603-33-8 triphenylbismuthane 

Downstream Products

• 15963-66-3 N-Chlor-N-benzolsulfonyl-cyclohexylamin 
• 41595-23-7 N-Cyclohexyl-N-(benzolsulfenyl)benzolsulfonamid 
• 200408-41-9 2,2'-diselenobis(N-cyclohexyl benzenesulfonamide) 
• 65299-65-2 N-Cyclohexyl-N,N-di(benzol)sulfonimid 
• 1620220-90-7 1-cyclohexyl-3-methyl-3-(tosylmethyl)indolin-2-one 
• 1620220-80-5 C₁₆H₂₁NO₃S 

Relevant academic research and scientific papers

Phosphine/Photoredox Catalyzed Anti-Markovnikov Hydroamination of Olefins with Primary Sulfonamides via α-Scission from Phosphoranyl Radicals

New strategies to access radicals from common feedstock chemicals hold the potential to broadly impact synthetic chemistry. We report a dual phosphine and photoredox catalytic system that enables direct formation of sulfonamidyl radicals from primary sulf

AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST

The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.

Copper(II)-Photocatalyzed N-H Alkylation with Alkanes

We report a practical method for the alkylation of N-H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)-H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N-H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.

A Versatile Electrochemical Batch Reactor for Synthetic Organic and Inorganic Transformations and Analytical Electrochemistry

A standardized and versatile electrochemical batch reactor that has wide applicability in both organic and inorganic synthesis and analytical electrochemistry has been developed. A variety of synthetic electrochemical transformations have been performed to showcase the versatility and demonstrate the reactor, including the synthesis of five Cu(I)-NHC complexes, two Au(I)-NHC complexes, and one Fe(II)-NHC complex as well as an Fe(III)-salen complex. The reactor is based on a commercially available vial with an adapted lid, making it inexpensive and highly flexible. It features a fixed interelectrode distance, which is crucial for reproducibility, along with the ability to accommodate a variety of interchangeable electrode materials. The reactor has also been used in conjunction with a parallel plate, allowing rapid screening and optimization of an organic electrochemical transformation. Cyclic voltammetry has been performed within the reactor on a range of imidazolium salt analytes with the use of an external potentiostat. The ability to use this reactor for both analytical and synthetic organic and inorganic chemistry is enabled by a flexible and characterizable design.

Hypervalent Iodine Mediated Sulfonamide Synthesis

A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.

Iron-Catalyzed Hydroamination and Hydroetherification of Unactivated Alkenes

The hydrofunctionalization of alkenes, explored for over 100 years, offers the potential for a direct, atom-economical approach to value-added products. While thermodynamically favored, the kinetic barrier to such processes necessitates the use of catalysts to control selectivity and reactivity. Modern variants typically rely on noble metals that require different ligands for each class of hydrofunctionalization, thereby limiting generality. This Letter describes a general iron-based system that catalyzes the hydroamination and hydroetherification of simple unactivated olefins.

Multicomponent synthesis of sulfonamides from triarylbismuthines, nitro compounds and sodium metabisulfite in deep eutectic solvents

A sustainable synthesis of sulfonamides using a copper-catalysed process starting from triarylbismuthines, Na2S2O5 and nitro compounds in a Deep Eutectic Solvent (DES) as a reaction medium is described. Thus, triarylbismuthines are used as reagents for the incorporation of SO2 into organic motifs. The bismuth salts formed as by-products can be easily removed from the crude reaction mixture by precipitation with water, while the use of volatile organic compounds (VOCs) as solvents can be avoided in the entire process. The eutectic mixture employed as the solvent is fully characterised, with the preliminary results proving its low toxicity. The designed DES also allows for a novel multicomponent reaction which saves time and reduces purification steps, energy and cost.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines

An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism.