3899-96-5

Upstream product

• 106-44-5 p-cresol 
• 98-59-9 p-toluenesulfonyl chloride 
• 142-45-0 Acetylenedicarboxylic acid 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 24045-96-3 2-iodo-4-methylphenyl-p-toluenesulfonate 
• 142207-58-7 Bis-4-methylphenyl acetylenedicarboxylate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 104-15-4 toluene-4-sulfonic acid 
• 108-88-3 toluene 
• 16188-57-1 2-iodo-4-methylphenol 
• 143674-28-6 10-(4'-methylphenyl)phenothiabismine 5,5-dioxide 

Downstream Products

• 65426-50-8 4-methyl-2-[(4-methylphenyl)sulfonyl]phenol 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 56506-60-6 N-(4-methylphenyl)hexylamine 
• 107271-15-8 1-phenyl-2-p-tolylpropan-1-one 
• 644-08-6 4-Methylbiphenyl 
• 106-44-5 p-cresol 
• 54879-64-0 N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 
• 112825-69-1 (4-methoxybenzyl)-p-tolylamine 
• 104-15-4 toluene-4-sulfonic acid 
• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 10504-92-4 N-p-xylyl-p-toluenesulfonamide 
• 33863-77-3 N-(4-methylbenzyl)-4-methylaniline 
• 53040-92-9 4-(4-tolyl)anisole 

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.

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

Double C-N bond cleavages of: N-alkyl 4-oxopiperidinium salts: Access to unsymmetrical tertiary sulfonamides

In this paper, regiospecific, double intraannular C-N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S-Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C-N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C-N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- A nd oxidant-free conditions.

Electron Donor-Acceptor Complex Enabled Decarboxylative Sulfonylation of Cinnamic Acids under Visible-Light Irradiation

Visible-light-induced decarboxylative sulfonylation of cinnamic acids with aryl sulfonate phenol esters enabled by the electron donor-acceptor complex is developed. The method offers a mild and green approach for the synthesis of vinyl sulfones with excellent functional group compatibility under photocatalyst and oxidant-free conditions.

LiCl-Accelerated Nickel Catalyzed Cross-Coupling of Aryl Tosylates with the Aryl Grignard Reagents

A mild coupling reaction catalyzed by Ni(acac)2-L4 has been studied. The catalyst acts efficiently in the reaction of biaryl coupling between various electrophiles and common or functionalized aryl Grignard reagents with high functional group tolerance. The study demonstrates that LiCl acts as an essential component in efficient cross-coupling by accelerating reduction of Ni(II) to Ni(0). The new catalytic system for selective couplings of aryl tosylates with aryl chlorides has been developed.

Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with p-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates

Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions.

Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water

A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.

Pd/Indanone-Based Ligands: An Efficient Catalyst System for Ullmann-Type, Suzuki-Miyaura, and Mizoroki-Heck Cross-Coupling Reactions with Aryl Tosylates and Aryl Halides

2-Hydroxyindan-1-ones have been efficiently synthesized and successfully applied as ligands in Pd-catalyzed Ullmann type, Suzuki-Miyaura, and Mizoroki-Heck cross-coupling reactions with aryl tosylates and aryl halides. The ligands are air- and moisture-stable and have shown high catalytic activity with Pd(OAc) 2 in these cross-coupling reactions. The system tolerates a variety of functional groups in the product and can be re-used at least three times with maximum efficiency..

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.