73178-10-6

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 104-15-4 toluene-4-sulfonic acid 
• 64846-47-5 4-nitrobenzene 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 

Downstream Products

• 959-22-8 p-nitrophenylbenzoate 
• 1310070-02-0 (4-methoxyphenyl)(4-nitrophenyl)iodonium p-toluenesulfonate 
• 102183-30-2 1,2,5-tri-(4-nitrophenyl)-1H-pyrazole 
• 1240390-04-8 (4-nitrophenyl)(2,4,6-trimethylphenyl)iodonium tosylate 

Relevant academic research and scientific papers

Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt-Derived Amphiphiles

Two sets of 19 amphiphiles derived from diaryliodonium salt in the form of 4-methylbenzenesulfonate salts and trifluoromethanesulfonate salts were synthesized in good yields through the oxidation of 17 different aryl iodides using oxone (potassium peroxymonosulfate) as the oxidation agent in Route I and meta-chloroperoxybenzoic acid as the oxidation agent in Routes II and III, followed by Friedel–Crafts reaction with (2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene to obtain the target compounds (1–19). Their structures were characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, and high-resolution mass spectrometry studies. Their surface activities were evaluated on the basis of surface tension and critical micelle concentration measurements by the Wilhelmy plate method at 25 °C. With their good water solubility, diaryliodonium salts (1–19) have excellent short-term bactericidal efficacy against Bacillus cereus in the concentration of 600 ppm at 20 °C. After compounding 1 or 18 with the broad-spectrum but skin-irritating antibacterial agent Kathon CG (methylchloroisothiazolinone in combination with methylisothiazolinone) in the ratio of 1:1 by mass, both formulations maintained lethality rate of >90% after 48 h.

Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts

A new synthetic method was developed for the N-arylation of pyrazoles using diaryliodonium salts. The transformation does not require any transition-metal catalyst and provides the desired N-arylpyrazoles rapidly under mild reaction condition in the presence of aqueous ammonia solution as a mild base without the use of inert atmosphere. The chemoselectivity of unsymmetric diaryliodonium salts was also explored with large number of examples.

Synthesis of ionic-liquid-supported diaryliodonium salts

The synthesis of ionic-liquid-supported diaryliodonium salts is described. The synthesis is simple and practical, and the ionic liquid products require no chromatographic purification. The ionic-liquid-supported diaryliodonium salts are quite stable, and they did not show any sign of decomposition or loss of reactivity, even after being stored for one month at 5 °C. The reactivity of these salts was explored in the phenylation of substituted phenols and carboxylic acids, and the corresponding diaryl ethers and aryl esters, respectively, were synthesized in good to excellent yields and with high purities.

Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts

An efficient arylation of carboxylic acids with diaryliodonium salts has been developed, giving aryl esters in high yields within short reaction times for both aromatic and aliphatic substrates. The transition-metal-free conditions are compatible with a range of functional groups, and good chemoselectivity is observed with unsymmetric diaryliodonium salts. Furthermore, steric hindrance in the ortho positions is well tolerated both in the carboxylic acid and in the diaryliodonium salt, yielding aryl esters that cannot be obtained via other esterification protocols.

Facile synthesis of Koser's reagent and derivatives from iodine or aryl iodides

The first one-pot synthesis of neutral and electron-rich [hydroxy(tosyloxy)iodo]arenes (HTIBs) from iodine and arenes is presented, thereby avoiding the need for expensive iodine(III) precursors. A large set of HTIBs, including a polyfluorinated analogue, can be obtained from the corresponding aryl iodide under the same conditions. The reaction proceeds under mild conditions, without excess reagents, and is fast and high-yielding. Together, the two presented routes give access to a wide range of HTIBs, which are useful reagents in a variety of synthetic transformations.

Structure of and Electronic Interactions in Aromatic Polyvalent Iodine Compounds: a 13C NMR Study

Available data on the structures, electronic substituent effects and 13C NMR spectra of aromatic polyvalent iodine compounds, particularly iodoso and iodoxy derivatives, are summarized and discussed.A series of aromatic tri- and penta-valent iodine compou

benzene, a Versatile Reagent for the Mild Oxidation of Aryl Iodides at the Iodine Atom by Ligand Transfer

Treatment of a variety of aryl iodides with benzene (1) under mild conditions resulted in ligand transfer, and new arenes were obtained.However, with some substrates containing proximate functional groups cyclic iodonium salts and iodinanes resulted.The reaction between 1 and 2-iodothiophene took a distinctly different course.