433-03-4

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 98-09-9 benzenesulfonyl chloride 
• 402-54-0 p-nitrobenzotrifluoride 
• 98-80-6 phenylboronic acid 
• 98-10-2 benzenesulfonamide 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 1089531-37-2 2-methyl-2-phenyl-N-(4-(trifluoromethyl)phenyl)propanamide 

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.

A Unified and Practical Method for Carbon–Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis

While carbon–heteroatom cross-coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C?O, C?N and C?S cross-coupling reactions under one general set of conditions. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel(II) complex, is responsible for the key reductive elimination step that couples aryl bromides, iodides, and chlorides to 1° and 2° alcohols, amines, thiols, carbamates, and sulfonamides, and is amenable to scale up via a flow apparatus.

Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.

Method for ultrasound-assisted synthesis of N-arylsulfonamide

The invention discloses a method for ultrasound-assisted synthesis of N-arylsulfonamide. N-arylsulfonamide compound is synthesized by series reaction of nitro reduction/sulfonyl chloride reduction/sulfonamidation with taking aromatic nitro compounds, sulfonyl chloride and iron powder as raw materials under ultrasonic stirring conditions. Water is used as a reaction medium and a hydrogen source inthe reaction. The method has the advantages of cheap and easily obtained raw materials, simple and mild reaction conditions, environmental friendliness, saving energy, high reaction selectivity and high yield, excellent compatibility of substrate functional groups and high application value.

Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates

A Pd(II)-catalyzed desulfitative arylation protocol between sulfonamides and sodium arylsulfinates was herein reported. The direct arylation reaction was successfully achieved by a Pd(II)/Ag(I)-mediated system without participation of any external ligands with a release of SO2. And different N-aryl sulfonamides were obtained readily in up to 86% yields, exhibiting good functional groups tolerance (25 examples).

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.

Visible Light-Induced Radical Rearrangement to Construct C-C Bonds via an Intramolecular Aryl Migration/Desulfonylation Process

A highly efficient intramolecular selective aryl migration/desulfonylation of 2-bromo-N-aryl-N-(arenesulfonyl)amide via visible light-induced photoredox catalysis has been accomplished. This approach allows for the construction of a variety of multisubstituted N,2-diarylacetamide under mild reaction conditions.

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.

Cu(OAc)2-catalyzed N-arylation of sulfonamides with arylboronic acids or trimethoxy(phenyl)silane

Cu(OAc)2-catalyzed C-N bond-formation reaction of sulfonamides with organoboronic acids or trimethoxy(phenyl)silane was achieved in the presence of 20mol% of Cu(OAc)2, providing N-arylation products with yields ranging from moderate to good.

Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-free conditions without using external base

Microwave-induced syntheses of sulfonamides, without using base under solvent-free conditions, have been developed. The process finds its utility because of its simple operational procedure and high yields. Moreover, the process is fast and accommodative to different substituents on aromatic as well as heteroaromatic rings rendering sulfonamides (28 examples).