24244-60-8

Usage

Uses

2-(Phenylsulfonyl)pyridine is a useful building block in organic synthesis.

InChI:InChI=1/C11H9NO2S/c13-15(14,10-6-2-1-3-7-10)11-8-4-5-9-12-11/h1-9H

Upstream product

• 24224-99-5 benzenesulfonyl cyanide 
• 123-73-9 trans-Crotonaldehyde 
• 126-73-8 phosphoric acid tributyl ester 
• 688-74-4 boric acid tributyl ester 
• 3111-54-4 2-phenylsulfanylpyridine 
• 109-09-1 2-chloropyridine 
• 873-55-2 sodium benzenesulfonate 
• 108-98-5 thiophenol 
• 109-04-6 2-bromo-pyridine 
• 98-80-6 phenylboronic acid 
• 5029-67-4 2-iodopyridine 
• 780-69-8 triethoxyphenylsilane 
• 4930-98-7 pyrid-2-ylhydrazine 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 1129-69-7 2-hexylpyridine 
• 14529-53-4 2-ethoxypyridine 
• 873-55-2 sodium benzenesulfonate 
• 71532-23-5 2-hex-5'-en-1'-ylpyridine 
• 1008-89-5 2-phenylpyridine 
• 4467-06-5 2-(4-methylphenyl)pyridine 
• 101-82-6 2-Benzylpyridine 
• 381725-49-1 2-methoxy-5-(pyridin-2-yl)pyridine 
• 1035920-14-9 (2-chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanol 
• 1242296-07-6 {2-([2-(2-chlorobenzoyl)phenyl]sulfonyl)pyridin-3-yl}(2-chlorophenyl)methanone 
• 1242296-08-7 (3-chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone 
• 1542796-07-5 2-((2R,3R)-3-(tert-butyl)-4-methoxy-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)pyridine 
• 1542796-11-1 2-((2R,3R)-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)pyridine 
• 1542796-14-4 2-((2R,3R)-4-(anthracen-9-yl)-3-(tert-butyl)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)pyridine 

Relevant academic research and scientific papers

Synthesis and antifungal activities of pyridine bioisosteres of a bismuth heterocycle derived from diphenyl sulfone

– Heterocyclic iodobismuthanes 7–9 [IBi(C6H4-2-SO2C5H3N-1′-)] derived from phenyl pyridinyl sulfones were synthesized. Their antifungal activities against the yeast Saccharomyces cerevisiae were compared with those of halobismuthanes [XBi(RC6H3-2-SO2C6H4-1′-)] (1: X=Cl; 2: X=I, R=H) derived from diphenyl sulfone derivatives to determine how the bioisosteric replacement of the benzene ring in 2 with the pyridine ring in 7–9 affects their activities. The antifungal activities of 7–9 were higher or comparable to those of 1 and 2. The DFT calculations suggested that the generation of the antifungal activity of the bismuthanes was well understood by the nucleophilic addition of methanethiolate anion as a model biomolecule at the bismuth atom to give an intermediate ate complex.

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides

The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.

A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling

An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.

Method for synthesizing sulfone compounds under photocatalysis condition

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

A [...] or heterocyclic sulfonamide compound preparation method (by machine translation)

The invention discloses a [...] or heterocyclic sulfonamide compounds of the preparation method, the [...] compound has the formula (I) of the structure shown, the heterocyclic and tissue compound has the formula (II) is shown in the structure, in an organic solvent under the condition of a portion of the inert gas, iodo aromatic ring compound and sodium hydrosulfite under heating conditions in the free radical coupling reaction to obtain the aromatic ring sulfinyl sodium intermediate, with the [...], or iodo alkane, or bromo alkane, or diaryl Iodized salt, or [...] reaction, obtained by the formula (I) has the structure shown as the [...], or formula (II) has the structure shown in the heterocyclic sulfonamide compounds. The method of the invention is simple and efficient, less side reaction, the product has high purity, facilitates separation of the purification, can be suitable for the preparation of a larger scale, with very good application prospect. (by machine translation)

Method for preparing heterocyclic sulfone or heterocyclic sulfamide compound

The invention belongs to the technical field of organic synthesis. The invention provides a method for preparing a heterocyclic sulfone or heterocyclic sulfamide compound. The method comprises the following steps: firstly, in a protection atmosphere, under the condition of visible light radiation, carrying out a free radical coupling reaction on an iodo-heteroaromatic compound, thiourea dioxide and sodium hydroxide so as to obtain aromatic heterocyclic sodium sulfinate, wherein a catalyst used in the free radical coupling reaction is fluorescein; and secondly, maintaining a protection atmosphere, carrying out an alkylation reaction or an amidation reaction on the aromatic heterocyclic sodium sulfinate and a group donor compound, thereby obtaining heterocyclic sulfone or heterocyclic sulfamide, wherein the group donor compound is a halogen compound, diaryl or an amino organic matter. The heterocyclic sulfone or the heterocyclic sulfamide can be prepared by only two steps of reactions byusing the method provided by the invention, and in addition, no strong corrosive substance is used, and the method is small in byproduct amount and high in yield.

Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines

We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium–1,1′-bis[(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium-catalyzed C–S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C–S coupling. We established herein that this choice of heteroaryl electrophilic reagent in palladium-catalyzed C–S bond formation allows overcoming palladium dithiolate out-of-cycle resting state inertness. This was illustrated in the stoichiometric reactivity study of the palladium dithiolate formed from 4-trifluoromethylbenzen-1-thiol –isolated and characterized by multinuclear NMR and XRD– with both 2-chloropyridine and 2-bromopyridine.

Ultrasonic-assisted green synthetic method for 2-sulfonyl pyridine derivatives

The invention discloses an ultrasonic-assisted green synthetic method for 2-sulfonyl pyridine derivatives. The 2-sulfonyl pyridine derivatives are synthesized from 2-halogenated pyridine compounds, sulfonyl chloride compounds and sulfite by one-pot reaction in an aqueous solution under the ultrasonic-assisted action. The raw materials are easily available, the reaction conditions are simple, mild,green and energy-saving, the reaction selectivity and yield are high, and compatibility of substrate functional groups is excellent; particularly, the 2-sulfonyl pyridine derivatives can be obtainedby filtering and direct separation, production cost is reduced, the problem of environmental pollution of the traditional method is solved, and the method has higher application value.

Convenient and Inexpensive Route to Sulfonylated Pyridines via S N Ar Reaction of Electron-Rich Pyridines by Iron Catalysis

Sulfonylated pyridines were synthesized in moderate to excellent yields, with a wide scope of substituted pyridines and sulfinate salts as starting materials, by an iron-catalyzed S N Ar reaction. This new methodology exhibits advantages for the synthesis of these useful substrates, such as the use of a readily available, inexpensive catalyst, prevention of the disproportionation of the sulfinate salts, and, more importantly, providing access to electron-rich pyridine substrates.