51238-46-1

Usage

Uses

Used in Organic Synthesis:
4-(phenylsulfanyl)benzonitrile is used as a building block in organic synthesis for the creation of a wide range of organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In pharmaceutical research, 4-(phenylsulfanyl)benzonitrile is utilized as a precursor in the synthesis of biologically active molecules. Its presence in the molecular structure can contribute to the development of new drugs with potential therapeutic applications.
Used in the Development of New Materials:
4-(phenylsulfanyl)benzonitrile has potential applications in the development of new materials due to its chemical properties. Its ability to participate in various chemical reactions can lead to the creation of innovative materials with unique properties.
Used as a Reagent in Chemical Reactions:
4-(phenylsulfanyl)benzonitrile also serves as a reagent in chemical reactions, facilitating specific transformations in organic chemistry. Its reactivity with other chemical entities makes it a useful tool in the synthesis of target molecules.
Used in Commercial Products:
4-(phenylsulfanyl)benzonitrile is found in some commercial products, indicating its practical applications in various industries. Its presence in these products underscores its importance in the manufacturing process and its contribution to the final product's properties.

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 13133-62-5 thiophenolate 
• 930-69-8 sodium thiophenolate 
• 52599-10-7 (4-bromo-phenyl)-phenylsulfanyl-diazene 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 17314-33-9 tributyltin phenyl sulfide 
• 111278-47-8 C₁₃H₉N₃S 
• 13435-20-6 tetraethylammoniumcyanide 
• 132555-11-4 (E)-(4-Cyanophenyl)azo phenyl sulfide 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 619-72-7 4-nitrobenzonitrile 
• 138373-10-1 4-cyanophenyl mesylate 

Downstream Products

• 100723-92-0 N’-hydroxy-4-(phenylthio)benzimidamide 
• 646517-01-3 C₃₀H₂₀N₂O₂S₂ 
• 850566-84-6 C₄₂H₅₂N₂O₂S₂ 
• 84212-05-5 4-phenylthiobenzylamine 
• 618909-31-2 4-(phenylsulfinyl)benzonitrile 
• 28525-13-5 4-(phenylsulfonyl)benzonitrile 
• 65085-83-8 4'-(phenylsulfonyl)acetophenone 
• 4779-37-7 2-bromo-1-(4-(phenylsulfonyl)phenyl)ethan-1-one 
• 2920-38-9 4-cyano-1,1'-biphenyl 

Relevant academic research and scientific papers

Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction

This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings

Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.

A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst

Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.

Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides

A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.

Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters

Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.

Aryl thioether compound and preparation method thereof

The invention discloses an aryl thioether compound and a synthesis method thereof, wherein an aryl carboxylic acid and a mercaptan (phenol) are used as main raw materials, and a nickel catalyst is prepared. Under the action of the phosphine ligand and the additive, the aryl carboxylic acid and the thiol (phenol) react in an organic solvent, and after the reaction is finished, the corresponding aryl thioether is obtained. The method has the advantages of low cost, high yield, simple and convenient operation, no pollution and the like, and has potential industrial application prospects. The method provides a cheap and green way for preparation of aryl thioether compounds.

Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

Photoactive electron donor-acceptor complex platform for Ni-mediated C(sp3)-C(sp2) bond formation

A dual photochemical/nickel-mediated decarboxylative strategy for the assembly of C(sp3)-C(sp2) linkages is disclosed. Under light irradiation at 390 nm, commercially available and inexpensive Hantzsch ester (HE) functions as a potent organic photoreductant to deliver catalytically active Ni(0) species through single-electron transfer (SET) manifolds. As part of its dual role, the Hantzsch ester effects a decarboxylative-based radical generation through electron donor-acceptor (EDA) complex activation. This homogeneous, net-reductive platform bypasses the need for exogenous photocatalysts, stoichiometric metal reductants, and additives. Under this cross-electrophile paradigm, the coupling of diverse C(sp3)-centered radical architectures (including primary, secondary, stabilized benzylic, α-oxy, and α-amino systems) with (hetero)aryl bromides has been accomplished. The protocol proceeds under mild reaction conditions in the presence of sensitive functional groups and pharmaceutically relevant cores.

Exploration of the mechanism and scope of the CuI/DABCO catalysed C–S coupling reaction

A cost effective and easily available CuI/DABCO catalytic system has been developed for the C–S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides, providing excellent yields and good chemoselectivity. We have also explored the mechanism of the reaction using DFT studies.

Pd (II) immobilized on clinoptilolite as a highly active heterogeneous catalyst for ullmann coupling-type s-arylation of thiols with aryl halides

Background: There are a number of protocols for Ullmann coupling–type S-arylation reactions, many of them suffer from the use of homogenous and often corrosive catalyst, cumbersome workup procedures, and long reaction times. Besides, many of these reagents are expensive and non-recoverable, leading to the generation of a large amount of toxic waste particularly when large-scale applications are considered. Objective: The aim of this study was to prepare a new Pd catalyst bonded on the surface of zeolite as a heterogeneous catalyst. Methods: A heterogeneous palladium catalyst has been prepared by immobilizing Pd ions on Clinoptilolite. This novel developed heterogeneous catalyst was thoroughly examined for Ullmann coupling–type S-arylation reaction using different bases, solvents and 0.003 mg of the catalyst. The structural and morphological characterizations of the catalyst were carried out using XRD, TGA, BET and TEM techniques. Results: Highly efficient heterogeneous palladium catalyst has been developed by immobilizing Pd ions on Clinoptilolite, as one of the most abundant naturally occurring zeolites for Ullmann S-arylation. By using this method, we provide an efficient way to a wide variety of substituted thiolic compounds. Moreover, the catalyst is easily recovered using simple filtration and reused for 5 consecutive runs. Conclusion: In this effort, we developed a new Pd catalyst bonded on the surface of zeolite as a substrate to prepare the heterogeneous catalyst. We demonstrate that this novel catalyst offers reliable and convincing data that may offer a valuable application in further developing the science and technology of Ullmann reaction protocols and allied industries. Additionally, the catalyst was reusable and kept its high activities over a number of cycles.