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• 623-00-7 4-bromobenzenecarbonitrile 
• 106-54-7 p-Chlorothiophenol 
• 623-03-0 4-Cyanochlorobenzene 
• 2863-98-1 4-hydrazinobenzonitrile hydrochloride 
• 619-72-7 4-nitrobenzonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 141212-57-9 5-p-(p-chlorophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole 
• 696-63-9 4-Methoxybenzenethiol 
• 1194-02-1 4-fluorobenzonitrile 
• 96461-98-2 4-(4-chlorophenylthio)benzoyl chloride 
• 18803-44-6 sodium p-chlorothiophenolate 

Downstream Products

• 80988-11-0 1-(4-chlorophenylsulfonyl)-4-cyanobenzene 
• 827610-57-1 4-(4-chlorophenylsulfanyl)benzylamine 

Relevant academic research and scientific papers

Synthesis of diaryl sulfides based on copper-doped OMS-2

We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material can be recycled several times.

Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen

Five new mononuclear tetra-coordinated zinc(ii) selones, [Zn(L1)2Cl2] (1), [Zn(L1)2Br2] (2), [{Zn(L2)4}{BF4}2] (3), [{Zn(L2)4}{ClO4}2] (4), and [Zn(L2)2Br2] (5), have been isolated from a one-pot reaction between the corresponding zinc(ii) salt and selone ligand, 1-methyl 3-naphthylmethylimidazoline-2-selone (L1) or 1-isopropyl 3-methylimidazoline-2-selone (L2). All these complexes were characterized by CHN analysis, FT-IR, NMR studies, and single-crystal X-ray crystallography techniques. The Zn(ii) center in 1-5 exhibits a distorted tetrahedral geometry. Besides, 1-5 were employed as catalysts in the thioetherification of aryl halides. The first zinc(ii) catalyst-mediated thioetherification of aryl halides without scrubbing oxygen was demonstrated. Catalysts 1-5 are highly active towards the cross-coupling reaction between aryl halides and thiophenols. The catalytic ability of 1-5 was explored in THF, toluene, and CH3CN solvents with different bases such as K2CO3, Cs2CO3, and NaOtBu. Interestingly, the zinc(ii) center attached to two selone ligands is much more catalytically active than that attached to four selone ligands.

Highly active mesoionic chalcogenone zinc(II) derivatives for C-S cross-coupling reactions

The first mesoionic heavier chalcogenones, L1-L3 [L1 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone; L2 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione; L3 = 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and π accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(ii) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(ii) chalcogenone complexes, [(L1)Zn(Cl)2(HOMe)] (1), [(L2)Zn(Cl)2(HOMe)] (3) and [(L2)Zn(Br)2(HOMe)] (4), and two dinuclear zinc complexes, [(L1)Zn(Br)(μ2-Br)]2 (2) and [(L3)Zn(Br)(μ2-Br)]2 (5), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes 1-5 represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(ii) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.

Method for synthesizing diarylthioether compound by using manganese oxide molecular sieve doped copper catalyst

The invention relates to a synthesis method of a diarylthioether compound by catalyzing with heterogeneous manganese oxide octahedral molecular sieve doped copper (Cu-OMS-2). The chemical structural formula of the compound is shown in the description, whe

Anionic Bismuth(III) chloride cluster with diselenide countercations: Application in C-S cross coupling reactions

The first weakly coordinating anion (WCA) with reactive p-block cation (rPBC) type of [(Bi4Cl16)4-{(LSeSeL)2+}2], L = 1,3-bis(2-benzhydryl-4,6-dimethylphenyl)-1H-imidazole-2(3H), ion pair is reported. The tetranuclear anionic bismuth(III) cluster shows a new type of ladder structure with two different types of Bi(III) coordination modes. In the solid state structure, the tetranuclear bismuth(III) cluster is sandwiched by two diselenide cations through hydrogen bonding interactions. Besides, this ion pair has been efficaciously employed as catalyst in C-S cross-coupling reactions under optimized reaction condition. This ion pair depicted a wide range of substrate scope with different thiols and aryl halides.

CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides

In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.

Electrochemically Promoted Nickel-Catalyzed Carbon-Sulfur Bond Formation

This work describes a nickel-catalyzed Ullmann-type thiolation of aryl iodidesunder mild electrochemical conditions. The simple undivided cell with graphene/nickel foam electrode setups offers excellent substrate tolerance, affording aryl and alkyl sulfides in good chemical yields. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated by cyclic voltammetry.

Visible-Light-Mediated Synthesis of Unsymmetrical Diaryl Sulfides via Oxidative Coupling of Arylhydrazine with Thiol

A metal-free visible-light-promoted oxidative coupling between thiols and arylhydrazines has been developed to afford diaryl sulfides using a catalytic amount of rose bengal as photocatalyst under aerobic conditions. A library of unsymmetrical diaryl sulfides with broad functionalities was synthesized in good yields at room temperature. The present methodology is also applicable to benzo[d]thiazole-2-thiols, benzo[d]oxazole-2-thiol, 1H-benzo[d]imidazole-2-thiols, and 1H-imidazole-2-thiol.

Tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex as an efficient and recyclable catalyst for coupling of aryl iodides with thiols

The C-S coupling reaction of aryl iodides with thiols was achieved at 110 °C in DMF/dioxane (V/V, 1:9) in the presence of a tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex [MCM-41-3OH-CuI] with Cs2CO3 as base to afford a variety of diaryl sulfides in good to excellent yields. The MCM-41-3OH-CuI catalyst can be easily recovered by a simple filtration and reused for at least six times without significant loss of activity.

Sulfanylphthalonitrile analogues as selective and potent inhibitors of monoamine oxidase B

It has recently been reported that nitrile containing compounds frequently act as potent monoamine oxidase B (MAO-B) inhibitors. Modelling studies suggest that this high potency inhibition may rely, at least in part, on polar interactions between nitrile functional groups and polar moieties within the MAO-B substrate cavity. In an attempt to identify potent and selective inhibitors of MAO-B and to contribute to the known structure-activity relationships of MAO inhibition by nitrile containing compounds, the present study examined the MAO inhibitory properties of series of novel sulfanylphthalonitriles and sulfanylbenzonitriles. The results document that the evaluated compounds are potent and selective MAO-B inhibitors with most homologues possessing IC50 values in the nanomolar range. In general, the sulfanylphthalonitriles exhibited higher binding affinities for MAO-B than the corresponding sulfanylbenzonitrile homologues. Among the compounds evaluated, 4-[(4-bromobenzyl)sulfanyl]phthalonitrile is a particularly promising inhibitor since it displayed a high degree of selectivity (8720-fold) for MAO-B over MAO-A, and potent MAO-B inhibition (IC50 = 0.025 μM). Based on these observations, this structure may serve as a lead for the development of therapies for neurodegenerative disorders such as Parkinson's disease.