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Relevant academic research and scientific papers

Visible-Light Photoredox-Catalyzed Aminosulfonylation of Diaryliodonium Salts with Sulfur Dioxide and Hydrazines

A photoredox-catalyzed three-component synthesis of N-aminosulfonamides starting from diaryliodonium salts, hydrazines and sulfur dioxide is reported. This reaction proceeds under mild conditions at room temperature and is driven by visible light. A simple bisulfite salt can be used as a readily available and easy-to-handle sulfur dioxide source. Mechanistic studies support a catalytic photoredox pathway with the diaryliodonium salt as convenient source for aryl radicals. (Figure presented.).

Metal-free aminosulfonylation of aryldiazonium tetrafluoroborates with DABCO×(SO2)2 and hydrazines

The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO 2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds smoothly at room temperature and shows broad functional-group tolerance. A radical process is proposed for this transformation. The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds under mild reaction conditions, is fast, has a broad substrate scope, and gives the products in high yiels (21 examples). A plausible mechanism that involves a radical process is also proposed. Copyright

Palladium-catalyzed aminosulfonylation of aryl iodides by using Na 2SO3 as the SO2 source

We realized an interesting palladium-catalyzed aminosulfonylation of aryl iodides by using Na2SO3 as a cheap SO2 source. In most cases, the yields were comparable to those reported by using the 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABCO·2SO 2, DABSO) as the SO2 source. Copyright

Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides

By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO 2 (1.2-2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.

A palladium-catalyzed reaction of aryl halides, potassium metabisulfite, and hydrazines

Aryl N-aminosulfonamides could be easily produced via a palladium-catalyzed coupling of aryl halides, potassium metabisulfite, and hydrazines. Potassium metabisulfite is an excellent equivalent of sulfur dioxide in the reaction of palladium-catalyzed aminosulfonylation. The Royal Society of Chemistry 2012.

Reactions of benzenesulfonohydrazides and benzenesulfonamides with hydrogen chloride or hydrogen bromide in acetic acid

Benzenesulfonohydrazides capable of yielding a sulfinic acid intermediate by virtue of a basic nitrogen atom in the second position of the hydrazide moiety produced thiosulfonates when treated with 1 N hydrogen chloride in acetic acid and produced disulfides when treated with 1 N hydrogen bromide in the same solvent. In two cases, a crystalline mixture of p-nitrophenyl p-nitrobenzenethiosulfonate and bis(p-nitrophenyl) disulfide was isolated from the hydrogen chloride reactions. No reaction product was obtained from either the hydrogen chloride or hydrogen bromide reaction with benzenesulfonohydrazides that were unable to form a sulfinic acid intermediate. Reduction of benzenesulfonamides to disulfides appeared to be possible only with hydrogen bromide in acetic acid. No thiosulfonate was isolated from the treatments of benzenesulfonamides with 1 N hydrogen chloride in acetic acid. p-Nitrophenyl p-nitrobenzenethiosulfonate and p-bromophenyl p-bromobenzenethiosulfonate exhibited some antimicrobial activities against Gram-positive bacteria. The latter compound also showed analgesic properties in the phenylquinone test.