446855-35-2

Upstream product

• 17849-38-6 2-Chlorobenzyl alcohol 
• 70-55-3 toluene-4-sulfonamide 
• 29281-83-2 4-methylbenzensulphonamide potassium salt 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 135822-90-1 o-chloro-N-tosylbenzaldimine 
• 10409-07-1 bis(4-methylphenyl)disulfone 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 

Downstream Products

• 127459-01-2 2,3-dihydro-2-[(4-methylphenyl)sulfonyl]-1H-isoindol-1-one 
• 135822-90-1 o-chloro-N-tosylbenzaldimine 
• 1427321-91-2 N-(2-chlorobenzyl)-N-(3-hydroxyprop-1-yn-1-yl)-4-methylbenzenesulfonamide 
• 1427321-72-9 3-[N-(2-chlorobenzyl)(4-methylbenzene)sulfonamido]prop-2-yn-1-yl2-[(tert-butoxycarbonyl)amino]acetate 
• 1427321-63-8 methyl 2-[(tert-butoxycarbonyl)amino]-3-[N-(2-chlorobenzyl)(4-methylbenzene)sulfonamido]penta-3,4-dienoate 

Relevant academic research and scientific papers

Amide Iridium Complexes As Catalysts for Transfer Hydrogenation Reduction of N-sulfonylimine

Sulfonamide moieties widely exist in natural products, biologically active substance, and pharmaceuticals. Here, an efficient water-soluble amide iridium complexes-catalyzed transfer hydrogenation reduction of N-sulfonylimine is developed, which can be carried out under environmentally friendly conditions, affording a series of sulfonamide compounds in excellent yields (96-98%). In comparison with organic solvents, water is shown to be critical for a high catalytic transfer hydrogenation reduction in which the catalyst loading can be as low as 0.001 mol %. These amide iridium complexes are easy to synthesize, one structure of which was determined by single-crystal X-ray diffraction. This protocol gives an operationally simple, practical, and environmentally friendly strategy for synthesis of sulfonamide compounds.

Diiodine-Triethylsilane System: Reduction of N-Sulfonyl Aldimines to N-Alkylsulfonamides

Because molecular iodine and hydrosilanes are stable to both air and moisture, reactions using these reagents are easy to operate and require mild reaction conditions. Molecular iodine and a hydrosilane were used to reduce N-sulfonyl aldimines to the corr

Method for synthesizing N-alkyl sulfonamide in water

The invention discloses a method for synthesizing N-alkyl sulfonamide in water, in particular to a method for synthesizing an N-alkyl sulfonamide derivative from a sulfonamide derivative and alcohol,and a water-soluble iridium complex is adopted to catalyze the reaction of N-alkyl sulfonamide. Compared with the previous synthesis method, the method has the advantages that a reaction equivalent substrate is used in the reaction process, so that raw material waste is avoided; weak base is used, and reaction conditions are mild; non-toxic and harmless pure water is used as a solvent in the reaction, only water is generated as a by-product, the atom reaction economy is high, and the requirement of green chemistry is met.

The: N -alkylation of sulfonamides with alcohols in water catalyzed by a water-soluble metal-ligand bifunctional iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2

The iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2 (Cp? = η5-pentamethylcyclopentadienyl, biimH2 = 2,2′-biimidazole) was synthesized and developed as a new-type of water-soluble metal-ligand bifunctional catalyst for the N-alkylation of poorly nucleophilic sulfonamides with alcohols in water. In the presence of catalyst (1 mol%) and Cs2CO3 (0.1 equiv.), a series of desirable products was obtained in 74-91% yields under microwave irradiation. Mechanistic experiments revealed that the presence of NH units in the imidazole ligand is crucially important for the catalytic activity of the iridium complex. Notably, this research would facilitate the process of water-soluble metal-ligand bifunctional catalysis for the hydrogen autotransfer process.

A bifunctional strategy for N-heterocyclic carbene-stabilized iridium complex-catalyzed: N -alkylation of amines with alcohols in aqueous media

Through the strategy of combining bifunctional 2-hydroxypyridine and a thermally stable N-heterocyclic carbene ligand, an Ir-catalyzed N-monoalkylation reaction has been developed in aqueous media under base-free conditions. This reaction proceeds smoothly with high yields of various aromatic amines and sulfonamides with a wide range of primary alcohols. Experimental and computational studies revealed a metal-ligand cooperative mechanism and its thermal stability during the bifunctional catalysis in aqueous media.

Synthetic method for preparing thiosulfonates on basis of sulfinic acid sodium salt disproportionated reaction

The invention relates to a synthetic method for preparing thiosulfonates on the basis of a sulfinic acid sodium salt disproportionated reaction. The preparation method comprises the steps that sulfinic acid sodium salts serve as the raw materials, boron trifluoride diethyl etherate serves as accelerant, dichloromethane serves as solvent, and by means of a disproportionation coupled reaction, a thiosulfinate compound with good biological activity is synthesized; two different sulfinic acid sodium salts serve as the raw materials, and by means of a crossed disproportionation coupled reaction method, an asymmetric thiosulfinate compound can be synthesized. By means of a one-pot method and a two-step method, and by means of a thiosulfonates intermediate prepared on site, a sulfones compound and a sulfonamides compound can be synthesized by directly starting from sulfinic acid sodium salts. Accordingly, a synthetic route for preparing thiosulfonates on the basis of the sulfinic acid sodiumsalt disproportionated reaction is provided for the first time, operation is easy, raw materials are easy to obtain, the condition is mild, no metal catalyst is needed, no additional oxidant or reductant is needed, and the prepared thiosulfonates can have the good biological activity, and can also serve as the intermediate of the reaction to be applied to organic synthesis.

Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3·OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates

The BF3·OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)2 bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.

A synthetic N-alkyl sulfonamide derivatives

The invention discloses a method for synthesizing a N-alkyl sulfonamide derivative. The method comprises the following steps: adding a sulfonamide derivative, a water-soluble catalyst, an alkali, alcohol and a solvent into a reaction container; reacting the reaction mixture at 100-120 DEG C for several hours, cooling to room temperature; performing rotary evaporation to remove the solvent, and then separating by a column to obtain the target compound. The method of the invention starts from the sulfonamide derivative, and obtains the N-alkyl sulfonamide derivative through reaction with alcohol. The method of the invention adopts a water-soluble iridium complex as a catalyst; the reaction is carried out in water; and the target compound is obtained with a high yield. Therefore, the reaction meets the requirements for green chemistry, and the method has wide development prospects.

The N-alkylation of sulfonamides with alcohols in water catalyzed by the water-soluble iridium complex {Cp*[6,6'-(OH)2bpy](H 2O)}[OTf]2

The water-soluble iridium complex {Cp*[6,6'-(OH)2bpy] (H2O)}[OTf]2 (Cp=ν5-pentamethylcyclopentadienyl, bpy=2,2'-bipyridine) was found to be a general and highly efficient catalyst for the Nalkylation of the poor nucleophilic sulfonamides with alcohols as alkylating agents in water. The presence of OH units in the bpy ligand is crucially important for the catalytic activity of the iridium complex. Mechanistic investigations revealed that the catalytically active species is a ligand-metal bifunctional iridium complex bearing an N,N'-chelated 2,2'-bipyridinated ligand and an aqua ligand. Notably, the present catalytic system and the proposed mechanism provide a new horizon and scope for the development of "hydrogen autotransfer (or hydrogen-borrowing) processes".

Highly efficient one-pot synthesis of N-alkyl sulfonamides from alcohols using N-(p-toluenesulfonyl) imidazole (Tsim)

A facile and efficient method for one-pot synthesis of N-alkyl sulfonamides from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this protocol, treatment of various potassium sulfonylamide salts and alcohols in the presence of TsIm and triethylamine in refluxing DMF furnishes the corresponding N-alkyl sulfonamides in good to excellent yields. This methodology is highly efficient for reaction of various structurally diverse primary and secondary alcohols as well as potassium sulfonylamides. Also, the density functional theoretical calculations are employed to mechanistically study this protocol. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]