90141-51-8

Upstream product

• 110-81-6 Diethyl disulfide 
• 98-56-6 4-chlorobenzotrifluoride 
• 74-86-2 acetylene 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 455-13-0 4-Iodobenzotrifluoride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 871362-15-1 bis(4-(trifluoromethyl)phenyl)iodonium trifluoromethanesulfonate 
• 17356-08-0 thiourea 
• 143028-36-8 4,4'-sulfinylbis((trifluoromethyl)benzene) 
• 696-62-8 para-iodoanisole 
• 13329-40-3 4-Iodoacetophenone 
• 108-86-1 bromobenzene 

Downstream Products

• 143028-36-8 4,4'-sulfinylbis((trifluoromethyl)benzene) 
• 368-43-4 phenylsulfonyl fluoride 
• 53451-90-4 phenyl 4-trifluoromethylphenyl sulfide 
• 53451-91-5 1-[(4-methoxyphenyl)thio]-4-(trifluoromethyl)benzene 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 

Relevant academic research and scientific papers

Palladium-catalysed thioetherification of aryl and alkenyl iodides using 1,3,5-trithiane as sulfur source

Thioetherification reaction of aryl iodides catalysed by palladium(II) complexes in the presence of 1,3,5-trithiane as sulphur source is reported. The paper presents the first homogeneous catalytic application of 1,3,5-trithiane in synthesis. Detailed optimization steps, the frames of the novel reaction are described, as well as the limitations and the substrate scope are also demonstrated. Moderate to good thioether yields were achieved in the presence of various substituted iodobenzenes and some alkenyl iodides, using palladium-xantphos catalyst system. Competitive reactions in the presence of mixed substrates were also performed and mechanistic considerations were assumed.

Heterogeneously Ni-Pd nanoparticle-catalyzed base-free formal C-S bond metathesis of thiols

This study rationally designed a heterogeneously catalyzed system (i.e., using Ni-Pd alloy nanoparticles supported on hydroxyapatite (Ni-Pd/HAP) under an H2atmosphere) achieving an efficient base-free formal C-S bond metathesis of various thiolsviasuppression of the Ni catalysis deactivation.

Coupling of thiols and aromatic halides promoted by diboron derived super electron donors

We have proven that pyridine-boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a SRN1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized polythioethers through a controlled and consecutive intramolecular electron transfer process.

Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides

A Bi-catalyzed synthesis of sulfonyl fluorides from the corresponding (hetero)aryl boronic acids is presented. We demonstrate that the organobismuth(III) catalysts bearing a bis-aryl sulfone ligand backbone revolve through different canonical organometallic steps within the catalytic cycle without modifying the oxidation state. All steps have been validated, including the catalytic insertion of SO2 into Bi-C bonds, leading to a structurally unique O-bound bismuth sulfinate complex. The catalytic protocol affords excellent yields for a wide range of aryl and heteroaryl boronic acids, displaying a wide functional group tolerance.

Scalable electrochemical reduction of sulfoxides to sulfides

A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.

Preparation of Recyclable and Versatile Porous Poly(aryl thioether)s by Reversible Pd-Catalyzed C–S/C–S Metathesis

Porous organic materials (polymers and COFs) have shown a number of promising properties; however, the lability of their linkages often limits their robustness and can hamper downstream industrial application. Inspired by the outstanding chemical, mechanical, and thermal resistance of the 1D polymer poly(phenylene sulfide) (PPS), we have designed a new family of porous poly(aryl thioether)s, synthesized via a mild Pd-catalyzed C–S/C–S metathesis-based method, that merges the attractive features common to porous polymers and PPS in a single material. In addition, the method is highly modular, allowing to easily introduce application-oriented functionalities in the materials for a series of environmentally relevant applications including metal capture, metal sensing, and heterogeneous catalysis. Moreover, despite their extreme chemical resistance, the polymers can be easily recycled to recover the original monomers, offering an attractive perspective for their sustainable use. In a broader context, these results clearly demonstrate the untapped potential of emerging single-bond metathesis reactions in the preparation of new, recyclable materials.

A Unified and Practical Method for Carbon–Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis

While carbon–heteroatom cross-coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C?O, C?N and C?S cross-coupling reactions under one general set of conditions. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel(II) complex, is responsible for the key reductive elimination step that couples aryl bromides, iodides, and chlorides to 1° and 2° alcohols, amines, thiols, carbamates, and sulfonamides, and is amenable to scale up via a flow apparatus.

B2cat2-Mediated Reduction of Sulfoxides to Sulfides

An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.

Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates

A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base-mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C?S bonds of triarylsulfonium cations to furnish the target products.

Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane

A disilathiane was found to be a novel S1 source for the copper-catalyzed synthesis of diaryl sulfides using aryl iodides. The reaction of iodoarenes and hexamethyldisilathiane, (Me 3 Si) 2 S, in the presence of a catalytic amount of CuI/1,10-phenanthroline provided various types of diaryl sulfides in good yields.