77189-88-9

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 5285-74-5 4-tolyl thiocyanate 
• 1516-28-5 allyl (p-tolyl)sulfide 
• 536-57-2 p-toluene sulfinic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 106-45-6 para-thiocresol 
• 39549-10-5 1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione 
• 98-59-9 p-toluenesulfonyl chloride 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 103-19-5 di(p-tolyl) disulfide 
• 933-00-6 p-methylbenzenesulfenyl chloride 

Relevant academic research and scientific papers

Metal-and oxidant-free electrochemical synthesis of aryl sulfides

A metal- and oxidant-free electrochemical synthesis of aryl sulfides was developed through a C–H sulfidation reaction of arenes and disulfides. Compared with traditional organic synthesis methods, this direct electrochemical approach efficiently generates aryl sulfides under catalyst- and oxidant-free conditions with the superiorities of wide substrate compatibility, mild reaction condition and waster free. At room temperature, various aryl thiols could be transformed smoothly in an undivided cell. Based on cyclic voltammetry (CV) and control experiments, the possible reaction mechanism was also proposed. The gram-scale synthesis emphasizes the practicability of this electrochemical strategy.

Transition-Metal-Free HFIP-Mediated Organo Chalcogenylation of Arenes/Indoles with Thio-/Selenocyanates

We have developed a protocol for the synthesis of diaryl thio-/selenoethers by the reaction of aryl chalcogenocyanates with electron rich arenes/hetero arenes via HFIP promoted C-H activation. The reaction produces chalcogenides in good to excellent yields under mild conditions without the need of a transition metal as a catalyst. The HFIP-mediated reactions tolerated a wide range of functional groups and set the stage for the synthesis of diversely decorated chalcogenides. A mechanism involving activation of the C-H bond through hydrogen bonding is proposed.

Scalable electrochemical reduction of sulfoxides to sulfides

A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.

Direct C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis

An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide

Electrochemical access to aryl sulfides from aryl thiols and electron-rich arenes with the potassium iodide as a mediator

An indirect electrooxidation method catalyzed by potassium iodide at a low potential for the synthesis of aryl sulfides from aryl thiols and electron-rich arenes has been developed. Cyclic voltammetry was carried out to investigate the electrocatalytic ac

Palladium(II)/Copper(II)-Catalyzed C–H Sulfidation or Selenation of Arenes Leading to Unsymmetrical Sulfides and Selenides

A novel palladium(II)/copper(II)-catalyzed sulfidation of the C–H bond in electron-rich arenes and in pentafluorobenzene with disulfides was developed. This catalytic system can be used to efficiently produce various types of either unsymmetrical aryl sulfides or alkyl aryl sulfides. The present protocol could also be applied to the direct preparation of unsymmetrical aryl selenides via C–H selenation.

Aerobic Oxidative Sulfenylation of Pyrazolones and Pyrazoles Catalyzed by Metal-Free Flavin-Iodine Catalysis

Two-component metal-free catalytic oxidative sulfenylation of pyrazolones with thiols has been achieved using the biomimetic flavin and iodine. The methodology is mild and eco-friendly, proceeds in the presence of air or molecular oxygen (1 atm) as the sole sacrificial reagent, and generates water as the only byproduct. The methodology was also extended to the sulfenylation of pyrazoles and electron-rich benzenes and afforded a series of thioethers in good yields.

Cu-catalyzed direct C-H thiolation of electron-rich arenes with arylsulfonyl hydrazides

An efficient Cu-catalyzed direct C–H thiolation of electron-rich arenes with arylsulfonyl hydrazides has been developed. Various mono(or bis)-thioether products were obtained in moderate to good yields. Mechanistic studies suggest that the reaction likely proceeds through free-radical formation including arylthio radical and sulfonyl radical, while both disulfanes and sulfonothioates are the major thiolation species in this transformation.

Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Synthesis of Aryl Sulfides in Water

An environmentally benign method for the synthesis of aryl sulfides in water under mild conditions has been realized, in which arenes are coupled with equal stoichiometry of allyl sulfides. This arylthiolation is enabled by the presence of the Lipshutz su