356031-47-5

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 98-59-9 p-toluenesulfonyl chloride 
• 527-60-6 Mesitol 
• 81388-53-6 2,4,6-trimethylphenoxide anion 
• 500127-97-9 C₁₁H₁₇N₃O₄S 

Downstream Products

• 1233691-85-4 3-(2,4,6-trimethylphenyl)-furan 
• 88-05-1 2,4,6-trimethylaniline 
• 39267-44-2 N-(p-tolyl)-2,4,6-trimethylaniline 
• 92-52-4 biphenyl 
• 3976-35-0 1-phenyl-2,4,6-trimethylbenzene 

Relevant academic research and scientific papers

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.

Copper-catalyzed intermolecular C-H amination of (Hetero)arenes via transient unsymmetrical λ3-iodanes

A one-pot two-step method for intermolecular C-H amination of electron-rich heteroarenes and arenes has been developed. The approach is based on a room-temperature copper-catalyzed regioselective reaction of the in situ formed unsymmetrical (hetero)aryl-λ3-iodanes with a wide range of primary and secondary aliphatic amines and anilines.

Suzuki-Miyaura coupling of aryl tosylates and mesylates in water

The palladium complex (0.5 mol-%) of a water-soluble sulfonated fluorenylphosphane (cataCXium Fsulf) enables the facile Suzuki-Miyaura coupling of various (heterocyclic) aryl tosylates and aryl mesylate with various (heterocyclic) boronic acids in excellent yields (> 95%) using water as the reaction solvent.

Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature

Mild palladium-catalyzed aminations of aryl tosylates and the first aminations of heteroaryl tosylates are described. In the presence of the combination of L2Pd(0) (L = P(o-tol)3) and the hindered Josiphos ligand CyPF-t-Bu, a variety of primary alkylamines and arylamines react with both aryl and heteroaryl tosylates at room temperature to form the corresponding secondary arylamines in high yields with complete selectivity for the monoarylamine. These reactions at room temperature occur in many cases with catalyst loadings of 0.1 mol % and 0.01 mol % in one case, constituting the most efficient aminations of aryl tosylates by nearly 2 orders of magnitude. This catalyst is made practical by the development of a convenient method to synthesize the L2Pd(0) precursor. This complex is stable to air as a solid. In contrast to conventional relative rates for reactions of aryl sulfonates, the reactions of aryl tosylates are faster than parallel reactions of aryl triflates, and the reactions of aryl tosylates are faster than parallel or competitive reactions of aryl chlorides. Copyright

Mild and efficient indium metal catalyzed synthesis of sulfonamides and sulfonic esters

A facile and efficient method for synthesizing sulfonamides was developed using a catalytic amount of indium metal. A wide range of sulfonamides were synthesized in excellent yields using the new process. The method showed a generality for substrates including less nucleophilic and sterically hindered anilines, and it is also applicable for preparing sulfonic esters from sulfonyl chlorides and alcohols. Georg Thieme Verlag Stuttgart.

Solvent-Free Synthesis of Aryl Tosylates under Microwave Activation

Synthesis of aryl tosylates from phenols requires only several minutes when conducted with controlled microwave heating under solvent-free condition. Eight different aryl tosylates were synthesized and isolated in good yields.

Preparation and reactivity of O2-sulfonated diazeniumdiolates

We report the facile preparation of O2-sulfonated diazeniumdiolates and mechanistic investigation of their reactions with representative nucleophiles. This new class of compounds extends the range of O2-substituted diazeniumdiolates available for potential applications in research and medicine.