59010-79-6

Upstream product

• 106-44-5 p-cresol 
• 108-98-5 thiophenol 
• 14204-24-1 N-(phenylthio)succinimide 
• 69120-23-6 (4-Methylphenyl)-pivaloat 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

Regioselective Ortho‐C–H sulfenylation of free phenols catalyzed by Co(II)-immobilized on silica-coated magnetic nanoparticles

Fe3O4?SiO2-UT?CoII is prepared by the silica-coated magnetic nanoparticles, urea-triazole, and CoCl2. This organic-inorganic hybride composite showed a good to excellent catalytic activity toward regioselective ortho-sulfenylation of free phenols and naphthols using pivalic anhydride as a directing group, also K2S2O8 and PPh3 were employed as oxidant and additive respectively. The newly synthesized catalyst was fully characterized by using different techniques such as FT-IR, TGA, DTG, TEM, SEM, EDS, ICP and VSM analyses. The competitive price, accessibility and lower toxicity of cobalt compared to expensive transition metals using for C–H bond activation and functionalization constitute precious advantages for this method. Moreover, this heterogeneous catalyst could be magnetically recovered and reused without significant loss of its catalytic activity after five cycles.

Co(II)-catalyzed regioselective clean and smooth synthesis of 2-(aryl/alkyl-thio)phenols via sp2 C-H bond activation

The first example of a smooth, practical and useful strategy for the preparation of ortho-aryl/alkyl sulfenyl phenols by using the reaction of aryl/alkyl thiols with phenols in the presence cobalt as catalyst, and with the assistance of acetic anhydride as directing group via C-H bond activation, was developed. Described method enables to form selectively C-S bond without any ligand, oxidant, and aryl/alkyl halide under mild conditions.

Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon-heteroatom bond formation

Catalytic cross-dehydrogenative coupling of heteroarenes with thiophenols and phenothiazines has been developed under mild and environmentally benign reaction conditions. For the first time, NOx+ was applied for catalytic C-S and C-N bond formation. A comprehensive scope for the C-H/S-H and C-H/N-H cross-dehydrogenative coupling was demonstrated with >60 examples. The sustainable cross-coupling conditions utilize ambient oxygen as the terminal oxidant, while water is the sole by-product.

Iron or boron-catalyzed C-H arylthiation of substituted phenols at room temperature

A simple, efficient and environmentally friendly method for iron or boron-catalyzed C-H arylthiation of substituted phenols at room temperature has been developed, and the corresponding diaryl sulfides were prepared in good to excellent yields. The protocol uses readily available 1-(substituted phenylthio)pyrrolidine-2,5-diones as the arylthiation reagents and inexpensive and environmentally friendly FeCl3 or BF3·OEt 2 as the catalyst, moreover no ligands, additives or extrusion of air are required, and the reactions can be performed successfully at room temperature. This journal is the Partner Organisations 2014.

Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides

A transition-metal-free synthetic method has been developed for the synthesis of unsymmetrical diaryl chalcogenides (S, Se, and Te) from diaryl dichalcogenides and arenes under oxidative conditions by using potassium persulfate at room temperature. Variously substituted arenes such as anisole, thioanisole, diphenyl ether, phenol, naphthol, di- and trimethoxy benzenes, xylene, mesitylene, N,N-dimethylaniline, bromine-substituted arenes, naphthalene, and diaryl dichalcogenides underwent carbon-chalcogen bond-forming reaction to give unsymmetrical diaryl chalcogenides in trifluoroacetic acid. To understand the mechanistic part of the reaction, a detailed in situ characterization of the intermediates has been carried out by 77Se NMR spectroscopy by using diphenyl diselenide as the substrate. 77Se NMR study suggests that electrophilic species ArE+ is generated by the reaction of diaryl dichalcogenide with persulfate in trifluoroacetic acid. The electrophilic attack of arylchalcogenium ion on the arene may be responsible for the formation of the aryl-chalcogen bond.

FeCl3-mediated direct chalcogenation of phenols

Direct sulfenylation and selenylation of phenols using a stoichiometric amount of FeCl3 under an oxygen atmosphere has been developed. The chalcogenated phenols were shown to be suitable for preparing S- and Se-containing compounds using the reaction of the remaining hydroxy group.