61209-69-6

Upstream product

• 529-36-2 1-Naphthalenethiol 
• 13407-53-9 naphthalene-1-sulfonyl azide 
• 98-80-6 phenylboronic acid 
• 64326-13-2 sodium naphthalene-1-sulfinate 
• 98-95-3 nitrobenzene 
• 13922-41-3 1-Naphthylboronic acid 
• 33397-22-7 tri(naphthalen-1-yl)bismuth 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Pyrene-sensitized photolysis of N-(1-naphthylsulfonyl)-N-phenyl-O-(p- toluoyl)hydroxylamine

The title hydroxylamine (SO2NT) underwent singlet-sensitized photolysis in the presence of pyrene to give rearrangement and fragmentation products. SO2NT was found to quench both pyrene-monomer and -excimer fluorescences. The presence of a sulfonyl group with a semipolar-bond character in SO2NT was suggested to be responsible for a pronounced termolecular interaction between the pyrene excimer and SO2NT to result in a quenching of the excimer emission. An energetic consideration of the pyrene monomer and excimer as well as the N-O bond cleavage of SO2NT allows us to propose that not the excimer, but the monomer, activates SO2NT to induce its sensitized decomposition. An analysis of the solvent polarity effects on both limiting the quantum yields for the appearance of the products and the quenching of pyrene fluorescence by SO2NT demonstrated that the sensitized reaction proceeds by a singlet-exciplex mechanism in benzene, whereas an electron- transfer mechanism predominates in acetonitrile.

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.

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.

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides

In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.

Synthesis of N-arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates

A novel one-step direct reductive coupling reaction between nitroarenes and sodium arylsulfinates was realized in the presence of an inexpensive Pd/C catalyst. In this procedure, readily available nitroarenes are employed as the nitrogen sources, and sodium arylsulfinates serve as both coupling partners and reductants. The method features high efficiency by using cheap Pd/C with low catalyst loading and good functional group tolerance in the absence of any additional reductants or ligands. This facile and mild synthetic method enables the high efficiency synthesis of functionalized N-arylsulfonamides from readily available substrates.

Copper-catalyzed Chan-Lam Coupling between Sulfonyl Azides and Boronic acids at room temperature

A mild and efficient method for the synthesis of N-arylsulfonamides in the presence of 10 mol % of CuCl is demonstrated. The reaction proceeds readily at room temperature in an open flask using a variety of sulfonyl azides and boronic acids without any base, ligand, or additive.

Solvent hydrogen bonding and structural effects on the reaction of biphenyl and naphthalene sulphonyl chloride with para-substituted anilines in dimethylformamide/acetonitrile mixtures

Substitution reactions of some of para-substituted anilines with biphenylsulphonyl chloride and naphthalenesulphonyl chloride were carried out conductometrically in dimethylformamide/acetonitrile mixtures. The correlation of second order rate constants wi

Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system

Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.

Mechanism of the Triplet-Sensitized Photolysis of N-(1-Naphthylsulfonyl)-N-phenyl-O-(p-toluoyl)hydroxylamine

The title hydroxylamine (SO2NT) undergoes triplet-sensitized photolysis in the presence of benzophenone (BP) or its derivative to give rearrangement and fragmentation products.Observations of the toluoyloxyl-migrated products, which are not obtained by the triplet-sensitized photolysis of N-(1-naphthoyl)-N-phenyl-O-(p-toluoyl)hydroxylamine (NT), indicate the occurrence of an efficient intersystem crossing of a triplet radical pair initially formed into a singlet radical pair.Internal heavy-atom-like effects of the partially charged sulfonyl sulfur and oxygen atoms are suggested to be responsible for this effective spin inversion.The finding that benzil, both the excited singlet and triplet states of which lie below those of SO2NT, causes a sensitized photolysis of this hydroxylamine to afford the same rearrangement and fragmentation products establishes the fact that a reaction sensitized by BP or its derivative proceeds through a triplet-exciplex intermediate.The effects of the solvent polarity and substituents of BP on the quantum yields for the reaction are discussed.