1576-48-3

Upstream product

• 62-53-3 aniline 
• 93-11-8 2-Naphthalenesulfonyl chloride 
• 13407-52-8 2-naphthalenesulphonyl azide 
• 98-80-6 phenylboronic acid 
• 1576-47-2 2-naphthalenesulphonamide 
• 873-55-2 sodium benzenesulfonate 
• 63735-42-2 sodium naphthalen-2-ylsulfinate 
• 98-95-3 nitrobenzene 
• 32316-92-0 naphthalene-2-boronic acid 
• 591-50-4 iodobenzene 

Downstream Products

• 542-11-0 aniline hydrobromide 
• 304694-54-0 ethyl 5-(naphthalene-2-sulfonamido)-2-phenylbenzofuran-3-carboxylate 
• 91-60-1 2-Naphthalenethiol 
• 106-47-8 4-chloro-aniline 

Relevant academic research and scientific papers

Preparation of acid-labile resins with halide linkers and their utility in solid phase organic synthesis

Mild and efficient preparation of acid-labile resins with displaceable halide linkers (3 and 4, X = Br and I) is described. These resins can be used in combinatorial organic synthesis of numerous drug-scaffold libraries. Their synthetic utility is exemplified by high yielding N-alkylations with structurally and electronically diverse sets of aliphatic and aromatic amines. Amongst the various resins modified and evaluated in this study, Wang resin derived bromo resin (3, X = Br) offers the best practical choice with respect to loading, stability, and chemical reactivity.

2-Naphthalenesulfonyl as a tosyl substitute for protection of amino functions. Cyclic voltammetry studies on model sulfonamides and their preparative cleavage by reduction

With the aim to develop a practically useful, reductively more labile alternative to tosyl for protection of amino functions, initially a number of N-arenesulfonyl-protected heterocycles (pyrroles, imidazoles, indole, and carbazole) have been prepared and

Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration

We describe a new strategy for aminoarylation of alkenes by copper-catalyzed smiles rearrangement using O-benzoylhydroxylamines as the amine reagent. This method affords various β-amino amide derivatives possessing a quaternary carbon center with wide functional group tolerance and high regioselectivity. The mechanistic studies indicate that the transformation can involve aminyl radical intermediates under acid-free condition.

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.

Copper-catalyzed synthesis of sulfonamides from nitroarenes: Via the insertion of sulfur dioxide

Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino, and carbonyl are all tolerated. A plausible mechanism is proposed, showing that arylsulfinate is the intermediate and the copper-assisted interaction of the nitroarene and arylsulfinate is the key step. This approach is also extended to the late-stage modification of a currently marketed drug (flutamide).

Synthesis method of sulfonamide compounds

The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of sulfonamide compounds. The structure of the compounds is characterized and confirmed by H NMR, C NMR. According to the method, 1-methyl-2-pyrrolidone is used as a solvent, tetrakis(acetonitrile) copper hexafluorophosphate/phenanthroline is used as a catalyst, isopropanol isused as a reducing agent, and phenylboronic acid, potassium metabisulfite and nitrobenzene are subjected to a reaction under a heating condition. The method comprises the following specific steps: reacting phenylboronic acid, potassium metabisulfite and the copper catalyst to generate a sulfinate intermediate, complexing the sulfinate intermediate with nitrobenzene under the action of copper, carrying out reductive deoxidation on the complex in virtue of isopropanol to obtain a hydroxylamine intermediate, and further reducing the hydroxylamine intermediate to obtain the sulfonamide compound.The preparation method of the compounds has the advantages that the preparation is started from nitrobenzene, so the step of reducing aromatic nitro compounds to obtain arylamine in a common preparation method is omitted; conditions are mild; the method is simple and efficient; sulfonyl chloride or sodium sulfinate reagents do not need to be synthesized in advance; compatibility of functional groups is high; and a wide range of substrates can be adopted.

A Versatile Synthesis of Vinyl-Substituted Heterocycles via Regio- And Enantioselective Pd-Catalyzed Tandem Allylic Substitution

We herein report a versatile, regio- and enantioselective palladium-catalyzed tandem allylic substitution powered by a chiral bisphosphorus ligand WingPhos with the palladium loading as low as 0.1 mol %, forming a series of chiral vinyl-substituted heterocycles, including tetrahydroquinoxalines, piperazines, dihydro-2H-benzo[b][1,4]-oxazines, and morpholines, in exellent ee's and yields. The protocol features readily available starting materials, mild reaction conditions, and a broad substrate scope. Mechanistic investigation supports a tandem allylic substitution process.

Synthesis of N-phenylsulfonamide derivatives and investigation of some esterase enzymes inhibiting properties

In this study, synthesis of nine N-phenylsulfonamide derivatives was designed by starting from aniline, which is the simplest aromatic amine. These compounds were obtained in yields between 69 and 95%. Inhibitory properties of synthesized compounds on car

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.

Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones

An alternative approach with eco-friendliness and high efficiency for the preparation of unsymmetrical diaryl sulfones has been developed. The strategy takes advantage of the reaction of sulfonyl hydrazides with quinone imine ketals catalyzed by DABCO (triethylenediamine) in ethanol. This transformation proceeds via a Lewis base promoted, direct 1,4-conjugate addition/sulfonylation/alcohol elimination reaction sequence. The protocol provides an efficient approach to access an array of diverse unsymmetrical diaryl and heterodiaryl sulfones, aryl alkyl sulfones and aryl vinyl sulfones in good to excellent yields.