54129-19-0

Upstream product

• 108-42-9 3-chloro-aniline 
• 98-09-9 benzenesulfonyl chloride 
• 98-10-2 benzenesulfonamide 
• 625-99-0 3-iodochlorobenzene 
• 121-73-3 3-Nitrochlorobenzene 
• 98-80-6 phenylboronic acid 
• 873-55-2 sodium benzenesulfonate 
• 108-37-2 1-bromo-3-chlorobenzene 

Downstream Products

• 117309-40-7 [Benzenesulfonyl-(3-chloro-phenyl)-amino]-acetic acid 
• 312-63-0 N-(4-fluorophenyl)benzenesulfonamide 
• 1678-25-7 N-phenylbenzenesulfonamide 

Relevant academic research and scientific papers

Sequential C-S and S-N Coupling Approach to Sulfonamides

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

Selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis

The selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis is described. The reaction tolerates a broad range of functional groups, and the desired products were obtained in 10–95% yield.

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Herein we report a highly efficient method for nickel-catalyzed C?N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C?N bond reductive elimination occurs from a triplet excited NiII complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.

Metal-free direct construction of sulfonamides via iodine- mediated coupling reaction of sodium sulfinates and amines at room temperature

A simple, practical, and metal-free protocol has been developed for the synthesis of sulfonamides from sodium sulfinates and various amines through an iodine-mediated SN bond formation reaction at room temperature. This green reaction is cost-effective, operationally straightforward, and especially proceeds under very mild conditions to afford the target products in good to excellent yields (up to 98%).

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature

A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is

Efficient manganese/copper bimetallic catalyst for N-arylation of amides and sulfonamides under mild conditions in water

An efficient and mild method using a bimetallic MnF2/CuI catalyst at 60 °C in water was developed for the N-arylation of amides and sulfonamides with aryl halides. A variety of functionalized amides and sulfonamides were coupled with different substituted aryl halides to afford the corresponding N-arylated products in good to excellent yields (up to 97 %). An efficient method using a bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane as the ligand has been developed for the cross-coupling of benzamides and sulfonamides with differently substituted aryl iodides in water. The corresponding N-arylated products were obtained in good to excellent yields (up to 97 %) under the catalytic conditions. Copyright

Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions

This Letter describes a copper catalyzed sulfonamide coupling reaction with aryl bromides to form N-aryl sulfonamides under mild conditions, including the first examples of Cu-catalyzed sulfonamide coupling at room temperature. The reaction protocol tolerates a broad range of substrates including a variety of primary and secondary sulfonamides and challenging heteroaryl bromides such as 2-bromothiazole.

Efficient ligand-free, copper-catalyzed N-arylation of sulfonamides

An efficient and convenient protocol has been developed for the N-arylation of sulfonamides with differently substituted aryl iodides using ligand-free copper iodide to afford the arylated products in good to excellent yields (up to 91%). Georg Thieme Verlag Stuttgart.

N- and 2-Substituted N-(Phenylsulfonyl)glycines as Inhibitors of Rat Lens Aldose Reductase

A variety of N-(phenylsulfonyl)-N-phenylglycines 5, N-(phenylsulfonyl)-2-phenylglycines 6, and N-(phenylsulfonyl)anthranilic acids 7 were prepared as analogues of the N-(phenylsulfonyl)glycine 1 aldose reductase inhibitors.In the rat lens assay, several derivatives of 5 display greater inhibitory activity than the corresponding glycines 1, suggesting that N-phenyl substitution enhances affinity for aldose reductase.Enzyme kinetic evaluations of the 4-benzoylamino analogues of 5 and 1 demonstrate that these compounds produce inhibition by the same mechanism.However, the significant differences in relative inhibitory potencies between compounds of series 5 and 1 may indicate that these compounds do not interact with the inhibitor binding site in precisely the same manner.Evaluation of the individual enantiomers of series 6 reveals that the S isomers are substantially more active than the corresponding R isomers.Also, with the exception of the naphthalene analogue 6n, the S stereoisomers of this series display greater inhibitory potencies than the glycines 1.The anthranilates 7 generally are less active than the glycines 1, demonstrating that direct incorporation of an aromatic ring in the glycine side chain may result in a decrease in affinity for aldose reductase.

Kinetische Verfolgung der Sulfamidbildung mittels quantitativer Differentialthermoanalyse

Die Reaktion zwischen Benzolsulfochlorid und einigen Anilinderivaten kann im Bereich oberchalb 200 K mit der dynamischen Technik der DTA untersucht werden, wobei sich eine Reaktion 2.Ordnung ergibt.Aktivierungsparameter und Reaktionsenthalpien werden durch die Anilinsubstituenten beeinflusst.