5633-56-7

Upstream product

• 6013-47-4 4-methylphenyl 4-methoxyphenyl sulfide 
• 536-57-2 p-toluene sulfinic acid 
• 108-95-2 phenol 
• 624-31-7 4-tolyl iodide 
• 637-89-8 4-sulfanylphenol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 106-45-6 para-thiocresol 
• 637-88-7 1,4-Cyclohexanedione 
• 540-38-5 p-Iodophenol 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 39549-10-5 1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione 
• 15015-57-3 bis(4-hydroxyphenyl)disulfide 

Downstream Products

• 1003960-06-2 tert-butyl 2-methyl-2-((4-p-tolylthio)phenyloxy)propanoate 

Relevant academic research and scientific papers

Site-Selective Synthesis of Aryl Sulfides via Oxidative Aromatization of Cyclohexanones with Thiophenols

We have introduced a metal-free facile access for the thiolation/aromatization of cyclohexanones with thiophenols to the corresponding aryl sulfides. The dehydroaromatic reaction of non-aromatic cyclohexanones proceeded smoothly using oxygen as a green oxidant.

Copper(II)-faciliated synthesis of substituted thioethers and 5-substituted 1H-tetrazoles: Experimental and theoretical studies

Benzoylhydrazine based Schiff base-ligated two new copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) were synthesized by the reaction of Cu(CH3COO)2·H2O with respective Schiff base ligand 1-[(4-nitrophenyl)ethylidene] benzohydrazide (HL1) or 1-[(4-methoxyphenyl)ethylidene] benzohydrazide (HL2). Both complexes were isolated as greenish solid and fully characterized by elemental analysis, FT-IR, EPR, thermo-gravimetric (TG) analysis and Cyclic Voltammetry. The molecular structures of both complexes have also been determined by single crystal X-ray crystallography, which confirmed the coordination of Schiff base ligands through N, O donor atoms and distorted square planar geometry around the Cu(II) ion. Both complexes were found to be good homogeneous catalysts for the synthesis of a wide range of substituted thioethers and 5-substituted 1H-tetrazoles in 92% and 93% yield, respectively, at a low catalyst loading (0.5 mol%). The bond angles and distances, as discerned from the DFT calculations, commusurated with the experimental findings. The energy difference between the HOMO and the LUMO, calculated from DFT studies, was found to be 5.645 eV and 6.459 eV for complex 1 and complex 2, respectively. These results are in harmony with the observed higher catalytic activity of complex 1.

Lewis Base/Bronsted Acid Dual-Catalytic C-H Sulfenylation of Aromatics

A Lewis base/Bronsted acid catalyzed aromatic sulfenylation is reported. These studies demonstrated that the incorporation of electron-rich sulfenyl groups proceeded in the absence of a Lewis base, with kinetic studies indicating an autocatalytic mechanism. The incorporation of electron-poor sulfenyl groups demonstrated little autocatalysis necessitating the use of a Lewis base. This method proved amenable to diverse arenes and heterocycles and was effective in the context of the late-stage functionalization of biologically active small molecules.

Modified conditions for copper-catalyzed ipso-thiolation of arylboronic acid esters with thiosulfonates

An efficient ipso-thiolation of arylboronic acid esters with thiosulfonates has been achieved under mild and odorless conditions using a copper catalyst. The use of TMEDA and cesium fluoride as the ligand and base, respectively, dramatically facilitated the desired transformation. The method exhibited a broad substrate scope, which allowed for the expeditious synthesis of diverse aryl sulfides from easily available starting materials.

Rhodium-catalyzed odorless synthesis of diaryl sulfides from borylarenes and: S -aryl thiosulfonates

Various diaryl sulfides, including heteroaryl- and nitrogen-containing sulfides, have been efficiently prepared by rhodium-catalyzed odorless deborylative arylthiolation of organoborons with S-aryl thiosulfonates. The ready availability of starting materials and further transformation of sulfides have rendered a diverse range of organosulfur compounds easily accessible.

Odorless, Regioselective Synthesis of Diaryl Sulfides and α-Thioaryl Carbonyls from Sodium Arylsulfinates via a Metal- Free Radical Strategy in Water

Regioselective arylthiolations of aromatic amines, arenols and ketones via C–H bond functionalization have been achieved with I2and PPh3in an aqueous system, whereby arylsulfenyl radicals are in situ generated from odorless sodium arylsulfinates. The arylsulfenyl radicals can react with free anilines containing electron-withdrawing groups and complex substrates (estrone and progesterone). Further experiments and quantum chemical calculations were also performed to deduce a mechanism for the formation of arylsulfenyl radicals. (Figure presented.).

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.

A highly efficient, ligand-free, and recyclable Cu2S-catalyzed coupling of aryl iodides with diaryl disulfides

A highly efficient and ligand-free copper(I) sulfide catalyzed cross-coupling reaction of aryl iodides with diaryl disulfides was developed. With only 1 mol-% of Cu2S as the catalyst, iron powder as the reductant, and K2CO3 as the base, aryl iodides reacted with disulfides in DMSO at 90-110 °C for 18-24 h under an atmosphere of argon to give the corresponding aryl sulfides in good to excellent yields. In addition, the catalyst is recyclable and reusable with some loss of activity.

SUBSTITUTED IMIDAZOLONE DERIVATIVES, PREPARATIONS AND USES

The present invention relates to polysubstituted imidazolone derivatives, to the pharmaceutical compositions comprising them and to the therapeutic uses thereof in the human and animal health fields. The present invention also relates to a process for preparing these derivatives.

Recyclable heterogeneous supported copper-catalyzed coupling of thiols with aryl halides: base-controlled differential arylthiolation of bromoiodobenzenes

Alumina-supported copper sulfate efficiently catalyzes the 5-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic halide. The catalyst is inexpensive, non-air sensitive, environmentally friendly and recyclable.