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Upstream product

• 392-56-3 Hexafluorobenzene 
• 53271-44-6 S-(4-methylphenyl) thio(4-methoxybenzoate) 
• 62525-84-2 4-Ethoxy-thiobenzoic acid S-p-tolyl ester 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 16956-91-5 2,3,5,6-tetrafluorophenylene-1,4-bis(trimethylsilane) 
• 103-19-5 di(p-tolyl) disulfide 
• 16495-78-6 (perfluorophenyl)(p-tolyl)sulfane 
• 363-72-4 Pentafluorobenzene 
• 106-45-6 para-thiocresol 
• 5745-36-8 4-methylphenyl dimethyldithiophosphinate 
• 53271-46-8 S-(p-tolyl) 3,5-dimethoxybenzothioate 

Relevant academic research and scientific papers

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.

The organocatalytic synthesis of perfluorophenylsulfides: Via the thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates

The organic superbase t-Bu-P4-catalyzed direct thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates was developed. Yields of perfluorophenylsulfides of up to 97% under catalysis of 5 mol% t-Bu-P4 were achieved. This method was shown to provide an efficient way to construct the perfluorophenyl-sulfur bond under mild metal-free reaction conditions. This journal is

The thiolation of pentafluorobenzene with disulfides by C-H, C-F bond activation and C-S bond formation

A metal-free thiolation reaction between pentafluorobenzene and disulfides by C-H, C-F bond activation and C-S bond formation is reported. Bisthiolated tetrafluorobenzene derivatives would be prepared in moderate to good yields from pentafluorobenzene and disulfides under mild conditions. A possible mechanism for the reaction was given.

Copper-catalyzed direct thiolation of pentafluorobenzene with diaryl disulfides or aryl thiols by C-H and C-F bond activation

A Cu-catalyzed cross-coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, tBuOLi or tBuOK as the base in DMSO at 60 °C under an O2 atmosphere was investigated. The corresponding bisarylthiola

Equilibrium shift in the rhodium-catalyzed acyl transfer reactions

Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio) pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes.

Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors

A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh 3)4-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6- tetrafluorobenzenes.

Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides: P-orientation in the polyarylthiolation of polyfluorobenzenes

In the presence of a catalytic amount of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene, an aromatic fluoride, an organic disulfide (0.5 equiv), and triphenylphosphine (0.5 equiv) reacted in refluxing chlorobenzene to give an aryl sulfide in high yield. Since triphenylphosphine trapped fluoride atoms forming phosphine difluoride, both organothio groups of the disulfide reacted effectively, and the fluoride substituent reacted more readily than the chloride and bromide. The reaction of hexafluorobenzene and a diaryl disulfide gave 1,4-diarylthio-2,3,5,6-tetrafluorobenzene, 1,2,4,5-tetraarylthio-3,6-difluorobenzene, and hexaarylthiobenzene in a stepwise manner; pentafluorobenzene gave 1-arylthio-2,3,5,6-tetrafluorobenzene; 1,2,3,4-tetrafluorobenzene gave 1,2-diarylthio-3,6-difluorobenzene; and 1,2,4,5-tetrafluorobenzene gave 1,4-diarylthio-2-5-difluorobenzene. The polyarylthiolation reaction of polyfluorobenzenes exhibited a strong tendency to form 1,4-difluorobenzenes. Copyright

THE THIOLATE ANION AS A NUCLEOPHILE. PART XIII. REACTIONS OF SOME TIN(II) AROMATIC THIOLATES

The reactions of tin(II) benzenethiolate and p-toluenethiolate with various fluoroaromatics in DMF have been studied.Replacement of some of the aromatic fluorines by the thiolate group was observed.The tin(II) aromatic thiolates are comparable in reactivity in these reactions with lead(II) benzenethiolate.All new compound have been characterized by elemental analysis, and NMR (H-1 and F-19) and mass spectroscopy.