1330786-68-9

Basic information

• Product Name: (3-trifluoromethylphenyl)(4-methoxyphenyl)iodonium p-toluenesulfonate
• Synonyms: (3-trifluoromethylphenyl)(4-methoxyphenyl)iodonium p-toluenesulfonate
• CAS NO: 1330786-68-9
• Molecular Weight: 550.337
• Mol File: 1330786-68-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3-trifluoromethylphenyl)(4-methoxyphenyl)iodonium p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (3-trifluoromethylphenyl)(4-methoxyphenyl)iodonium p-toluenesulfonate(1330786-68-9)
• EPA Substance Registry System: (3-trifluoromethylphenyl)(4-methoxyphenyl)iodonium p-toluenesulfonate(1330786-68-9)

Safety Data

• Hazardous Substances Data: 1330786-68-9(Hazardous Substances Data)

Upstream product

• 100-66-3 methoxybenzene 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 104-15-4 toluene-4-sulfonic acid 
• 41018-60-4 (3-(trifluoromethyl)phenyl)-λ3-iodanediyl diacetate 

Downstream Products

• 557780-43-5 4-methoxy-N-morpholinobenzenesulfonamide 
• 2715-05-1 1-(trifluoromethyl)-3-(phenylsulfonyl)benzene 
• 403-82-7 2,4-dimethylphenyl(3-trifluoromethylhenyl) ether 

Relevant articles and documents

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides

Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.

Metal-free arylation of oxygen nucleophiles with diaryliodonium salts

Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho- and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy. Copyright