3955-72-4

Usage

InChI:InChI=1/C14H14O3S/c1-11-6-8-14(9-7-11)18(15,16)17-13-5-3-4-12(2)10-13/h3-10H,1-2H3

Upstream product

• 108-39-4 3-methyl-phenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 23297-05-4 5-methyl-2-[(4-methylphenyl)sulfonyl]phenol 
• 23157-97-3 3-methyl-4-[(4-methylphenyl)sulfonyl]phenol 
• 643-93-6 3-methylbiphenyl 
• 108123-16-6 3-methoxy-4-(toluene-4-sulfonyl)-toluene 
• 17171-17-4 4'-methoxy-3-methylbiphenyl 
• 14625-58-2 2-(3-methylphenyl)benzoxazole 
• 7383-90-6 3,4'-dimethylbiphenyl 
• 223799-24-4 2-(3-methyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane 
• 620-22-4 3-Methylbenzonitrile 
• 15286-13-2 diethyl (m-tolyl)phosphonate 
• 6840-27-3 (3-methylphenyl)diphenylphosphine oxide 
• 4385-67-5 3-(3-methylphenyl)pyridine 
• 1432998-28-1 C₁₃H₁₃N 
• 3111-77-1 di-m-tolyl sulfide 

Relevant academic research and scientific papers

Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols

A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.

The Synthesis and Catalytic Activity of New Mixed NHC-Phosphite Nickel(0) Complexes

Herein we describe the synthesis and isolation of the first low-valent NHC-phosphite nickel complexes of general formula Ni(NHC)[P(OAr)3]2. These three-coordinate Ni(0) compounds were fully characterized, including by X-ray crystallography that highlighted their trigonal planar geometry. The representative complex Ni(IMes)[P(OPh)3]2 was used to show that a phosphite ligand is readily substituted in the presence of an aldehyde or nitrile. These stoichiometric studies then led to an investigation of their catalytic properties in the Suzuki-Miyaura cross-coupling reactions between aryl tosylates and aryl boronic acids, a first for such a NHC-Ni catalyst. Finally, mechanistic investigations led to the isolation of a well-defined oxidative addition product.

Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source

Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.

METAL OXIDE CATALYZED RADIOFLUORINATION

Inter alia, the first titania-catalyzed [18F]-radiofluorination in highly aqueous medium is provided. In embodiments, the method utilizes titanium dioxide, 1 : 1 acetonitrile- thexyl alcohol solvent mixture and tetrabutylammonium bicarbonate as a base. Radiolabeling may be directly performed with aqueous [18F]fluoride without the need for drying/azeotroping step, which reduces radiosynthesis time while keeping high fluoride conversion. The general applicability of the synthetic strategy to the synthesis of the wide range of PET probes from tosylated precursors is demonstrated.

Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates

Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding

Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium

Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [18F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this report, we demonstrate the possibility of 18F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile-thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [18F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. The substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.

Iodine-induced synthesis of sulfonate esters from sodium sulfinates and phenols under mild conditions

An iodine-induced synthesis of sulfonate esters via cross-coupling reactions of sodium sulfinates with phenols is reported. This synthetic route is low-cost, facile, green and efficient, and could afford the target products with good to excellent yields u

Nickel-catalyzed C-P coupling of aryl mesylates and tosylates with H(O)PR1R2

A method was developed for the nickel-catalyzed phosphonylation of aryl mesylates and tosylates with H(O)PR1R2. To the best of our knowledge, this is the first example of nickel-catalyzed C-P coupling of aryl mesylates and tosylates. Most of the substrates gave moderate to good yields under our catalytic system.

Neopentylglycolborylation of aryl mesylates and tosylates catalyzed by Ni-based mixed-ligand systems activated with Zn

(Chemical Presented) The mixed-ligand system NiCl2(dppp)/dppf is shown to be an effective catalyst for the neopentylglycolborylation of ortho-, meta-, and para-substituted electron-rich and electrondeficient aryl mesylates and tosylates. The ad

Highly efficient Pd-catalyzed cyanation of aryl chlorides and arenesulfonates with potassium ferrocyanide in aqueous media

A highly improved Pd-catalyzed cyanation of aryl chlorides to corresponding benzonitriles was demonstrated in aqueous media. Moreover, Pd-catalyzed cyanation of aryl tosylates and benzenesulfonates with K4[Fe(CN) 6] was developed under the similar conditions, which extended application scope of the cyanation. Graphical Abstract: [Figure not available: see fulltext.]