194359-22-3

Upstream product

• 39549-10-5 1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione 
• 13331-27-6 m-nitrobenzene boronic acid 
• 645-00-1 m-iodonitrobenzene 
• 106-45-6 para-thiocresol 
• 38078-55-6 sodium S-(4-methylphenyl) thiosulfate 
• 99-65-0 meta-dinitrobenzene 

Downstream Products

• 141573-12-8 p-methylphenyl m-nitrophenyl sulfone 

Relevant academic research and scientific papers

A water soluble Ni-Schiff base complex for homogeneous green catalytic C[sbnd]S cross-coupling reactions

Since the embarkation of C[sbnd]S cross-coupling from aryl halides with thiols a handful of works have been contemplated in aqueous medium. Herein, we report an example of a water soluble Ni-Schiff base complex as the green catalyst for the synthesis of t

C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.

PHOTOCATALYST-FREE, LIGHT-INDUCED CARBON-SULFUR CROSS-COUPLING METHODS

In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.

An aryl thioether synthetic method of the compound

The invention discloses a synthetic method of an aryl sulfide type compound shown by a formula (3). In a reaction solvent, an aryl or alkenyl thiosulfate type derivative and a boric acid, boric acid grease or borate type derivative are used as reaction raw materials and react with each other to obtain a polysubstituted aryl sulfide type compound under the action of a metal copper catalyst. According to the synthetic method disclosed by the invention, reaction conditions are mild, raw materials are easily-available and low in price, the reaction operation is simple, the yield is relatively high, and a key skeleton structure is provided for the synthesis of many natural products and medicaments, so that the method can be widely applicable to industrial scale production. A formula is shown in the specification.

Visible-light-promoted C-S cross-coupling via intermolecular charge transfer

Disclosed is a mild, scalable, visible-lightpromoted cross-coupling reaction between thiols and aryl halides for the construction of C-S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C-S coupling protocol was applied in drug synthesis and latestage modifications of active pharmaceutical ingredients. UV-vis spectroscopy and time-dependent density functional theory calculations suggest that visible-lightpromoted intermolecular charge transfer within the thiolate-aryl halide electron donor-acceptor complex permits the reactivity in the absence of catalyst.

CO2-promoted oxidative cross-coupling reaction for C-S bond formation via masked strategy in an odourless way

Cu-catalyzed direct oxidative cross-coupling between boronic acids and masked sulfides delivering thioethers was described, in which the SO3-, as a mask, has shown a distinctive effect on the oxidative cross-coupling condition. Disulfide could be suppressed efficiently via masked strategy under CO2 atmosphere. A broad scope of aromatics and scalable processes indicates its practicality, which could be further applied to drug late-stage modification and unsymmetrical dibenzothiophenes (DBTs) synthesis.

CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: Scope and mechanism

CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs 2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.

Microwave efficient S-arylation of thiols with aryl iodides using supported metal nanoparticles

An efficient and green microwave-assisted heterogeneous S-arylation protocol, reported for the first time, provided excellent coupling conversions and selectivities in minutes of reaction using Fe (homocoupling) and Cu (cross-coupling) supported metal nanoparticles.

A reusable FeCl3·6H2O/cationic 2,2′-bipyridyl catalytic system for the coupling of aryl iodides with thiols in water under aerobic conditions

In this study, an FeCl3·6H2O/cationic 2,2′-bipyridyl system was employed as a catalyst in the coupling of aryl iodides with thiols to form an aryl-sulfur bond in refluxed water under aerobic conditions. The residual aqueous solution after extraction could be reused for several cycles without a significant decrease in activity.

A mild, nonbasic synthesis of thioethers. The copper-catalyzed coupling of boronic acids with N-thio(alkyl, aryl, heteroaryl)imides

(equation presented) A new synthesis of thioethers is described. The reaction of boronic acids with aryl, heteroaryl, and alkyl N-thioimides in the presence of catalytic quantities of a Cu(I) carboxylate affords good to excellent yields of thioethers. This reaction takes place in the absence of a base under mild conditions (THF, 45-50°C, 2.5-12 h) and represents an interesting complement to known methods for thioether synthesis.