51954-54-2

Upstream product

• 4783-68-0 2-phenoxypyridine 
• 106-45-6 para-thiocresol 
• 109-04-6 2-bromo-pyridine 
• 109-09-1 2-chloropyridine 
• 4262-06-0 di-2-pyridyl sulfide 
• 5029-67-4 2-iodopyridine 
• 2637-34-5 2-Sulfanylpyridine 
• 2127-03-9 2,2'-dipyridyldisulphide 
• 624-31-7 4-tolyl iodide 
• 142-08-5 2-hydroxypyridin 
• 5720-05-8 4-methylphenylboronic acid 
• 65007-00-3 pyridin-2-yl trifluoromethanesulfonate 
• 57785-86-1 pyridin-2-yl tosylate 
• 3847-19-6 2-acetoxypyridine 

Downstream Products

• 1008-89-5 2-phenylpyridine 
• 581-50-0 2,3'-bipyridine 
• 366-18-7 [2,2]bipyridinyl 
• 10273-88-8 3-methyl-2,2'-bipyridine 
• 205052-93-3 6-bromo-4-methoxy-2,2'-bipyridine 
• 56100-22-2 6-methyl-2,2'-bipyridine 
• 381725-49-1 2-methoxy-5-(pyridin-2-yl)pyridine 
• 52258-16-9 4-methylphenyl 2-naphthyl sulfide 
• 643-93-6 3-methylbiphenyl 
• 1370652-74-6 1,2-bis(5-methylbiphenyl-2-yl)disulfane 
• 1289560-30-0 2-{4-methyl-2-[(E)-styryl]phenylsulfinyl}pyridine 
• 1289560-29-7 (E)-butyl 3-(5-methyl-2-(pyridin-2-ylsulfinyl)phenyl)acrylate 
• 1279130-27-6 5-methyl-2-(2-pyridinylsulfinyl)phenyl acetate 
• 1279130-28-7 5-methyl-2-(2-pyridinylsulfinyl)-1,3-phenylene diacetate 

Relevant academic research and scientific papers

Convenient MW-assisted synthesis of unsymmetrical sulfides using sulfonyl hydrazides as aryl thiol surrogate

An efficient synthesis of unsymmetrical sulfides has been achieved via the cross-coupling reaction of aryl/het-aryl/benzyl halides with stable and easily workable sulfonyl hydrazides as thiol substitutes by means of [DBU][HOAc] and CuI under microwave irr

Thiolate-assisted copper(i) catalyzed C-S cross coupling of thiols with aryl iodides: scope, kinetics and mechanism

Transition metal catalyzed coupling of thiols with aryl iodide offers a convenient method for accessing C-S linkage in organic synthesis. Herein, we report an efficient and practical method for the C-S cross coupling of thiophenols with aryl iodides using a Cu(i) catalyst. A diverse set of thiophenols is coupled with electron rich and poor aryl iodides to obtain diaryl sulfides in good to excellent yields. Noteworthily, these reactions proceed smoothly in polar protic solvents and under ligand-free environments. This procedure also finds application in the synthesis of 2-aminophenyl sulfide derivatives via ring opening of readily available benzothiazole. Furthermore, we performed kinetics and computational studies to understand the mechanism of the Cu(i) catalyzed reaction in the absence of a ligand. Hammett plots of the reaction rates versus the substituent constant show that these coupling reactions are modestly sensitive to the substituents on thiophenols as well as aryl iodides, indicating the involvement of both the reactants in the rate-determining step of the reaction. On the other hand, computational investigations of the different mechanistic pathways suggest that the strong coordination of thiolate to Cu may generate the catalytically competent intermediate [Cu(SPh)2]K which can initiate the catalytic cycle. The pathway initiated by [Cu(SPh)2]K is predicted to proceed through the lowest energy transition states and intermediates relative to the separated reactants.

Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides

A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.

2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed C-H Olefination of Arenes with Molecular Oxygen as the Sole Oxidant

Pd(II)-catalyzed C-H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulf

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst

We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.

Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides

Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO2R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical conditions, broad substrate scope, and excellent tolerance.

Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines

An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.

Direct C-S bond formation: Via C-O bond activation of phenols in a crossover Pd/Cu dual-metal catalysis system

A dual-metal catalysis system including a newly prepared nanoparticle [SiO2@organic-linker(OL)@Pd(II)] and CuI was introduced with ultra-high catalytic activity (high turnover number (TON), up to 19000) to a one-pot and odorless synthesis of unsymmetrical aryl sulfides by crossover C-S bond formation. The reaction proceeds via C-O bond activation of phenols and direct C-S bond formation in the presence of S8 as an oddorless sulfur source and aryl boronic acids under mild conditions (room temperature). The catalyst could be recycled up to five times without an obvious change in its activity.

NiFe2O4 as a magnetically recoverable nanocatalyst for odourless C–S bond formation via the cleavage of C–O bond in the presence of S8 under mild and green conditions

We present green methodologies for one-pot and odourless syntheses of unsymmetric and symmetric diaryl sulfides via C─O bond activation using NiFe2O4 magnetic nanoparticles as a reusable heterogeneous nanocatalyst. The synthesis of unsymmetric sulfides is performed using the cross-coupling reaction of phenolic esters such as acetates, triflates and tosylates with arylboronic acid/S8 or triphenyltin chloride/S8 as thiolating agents in the presence of base and NiFe2O4 magnetic nanoparticles as a catalyst in poly(ethylene glycol) as solvent at 60–85°C. Also, the synthesis of symmetric diaryl sulfides from phenolic compounds using S8 as the sulfur source and NiFe2O4 as catalyst in dimethylformamide at 120°C is described. Using these protocols, the syntheses of various unsymmetric and symmetric sulfides become easier than using the available protocols due to the use of a magnetically reusable bimetallic nanocatalyst and avoiding the use of thiols and aryl halides.

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.