27126-77-8

Upstream product

• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 100-66-3 methoxybenzene 
• 591-50-4 iodobenzene 
• 126550-93-4 <(hydroxy)(tosyloxy)iodo>-p-methoxybenzene 
• 104-15-4 toluene-4-sulfonic acid 
• 71-43-2 benzene 
• 696-62-8 para-iodoanisole 

Downstream Products

• 462-06-6 fluorobenzene 
• 613-37-6 4-methoxylbiphenyl 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 3857-04-3 [18F]fluorobenzene 
• 115298-63-0 phenyl(4-methoxyphenyl)iodonium triflate 
• 93-99-2 benzoic acid phenyl ester 
• 1523-19-9 4-methoxyphenyl benzoate 
• 1655-68-1 1-methoxy-3-phenoxybenzene 
• 58005-59-7 4-methyl-3'-methoxy-diphenyl ether 
• 3661-49-2 3-methoxy-N-(4-methoxyphenyl)benzenamine 
• 101-16-6 3-methoxy-N-phenylaniline 
• 74610-81-4 methyl-(4-methoxyphenyl)-propanedioic acid ethyl diester 
• 34009-61-5 diethyl 2-methyl-2-phenylmalonate 
• 519-87-9 N,N-diphenylacetamide 

Relevant academic research and scientific papers

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.

METHOD FOR SYNTHESIZING IODO- OR ASTATOARENES USING DIARYLIODONIUM SALTS

The present invention concerns a method of synthesizing a iodo- or astatoarene comprising the reaction of a diaryliodonium compound with a iodide or astatide salt, respectively. The invention also relates to said iodo- or astatoarene and diaryliodonium co

Pd(0)-Mediated 11C-Carbonylation of Aryl(mesityl)iodonium Salts as a Route to [11C]Arylcarboxylic Acids and Derivatives

Pd(0)-mediated 11C-carbonylation of aryl(mesityl)iodonium salts followed by suitable quench provides a rapid room-temperature two-pot procedure for labeling arylcarboxylic acids and amide derivatives with the short-lived positron emitter carbon

Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts

Aryliodonium salts have become precursors of choice for the synthesis of18F-labeled tracers for nuclear imaging. However, little is known on the reactivity of these compounds with heavy halides, that is, radioiodide and astatide, at the radiotracer scale. In the first comparative study of radiohalogenation of aryliodonium salts with125I?and211At?, initial experiments on a model compound highlight the higher reactivity of astatide compared to iodide, which could not be anticipated from the trends previously observed within the halogen series. Kinetic studies indicate a significant difference in activation energy (Ea=23.5 and 17.1 kcal mol?1with125I?and211At?, respectively). Quantum chemical calculations suggest that astatination occurs via the monomeric form of an iodonium complex whereas iodination occurs via a heterodimeric iodonium intermediate. The good to excellent regioselectivity of halogenation and high yields achieved with diversely substituted aryliodonium salts indicate that this class of compounds is a promising alternative to the stannane chemistry currently used for heavy radiohalogen labeling of tracers in nuclear medicine.

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.

Metal-free n -arylation of secondary amides at room temperature

The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.

Arylation with unsymmetrical diaryliodonium salts: A chemoselectivity study

Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new "anti-ortho effect" has been identified in the arylation of malonates. Several "dummy groups" have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents. Copyright

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

Fluoroalcohols: Versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) salts

We first introduced 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as unique solvents for reactions involving hypervalent iodine-mediated phenolic oxidations in the 1980s, in which the fluoroalcohols have been successfully utili

One-pot synthesis of diaryliodonium salts using toluenesulfonic acid: A fast entry to electron-rich diaryliodonium tosylates and triflates

A direct synthesis of symmetric and unsymmetric electron-rich diaryliodonium salts is described. The use of MCPBA and toluenesulfonic acid delivers diaryliodonium tosylates in high yields. An in situ anion exchange has also been developed, giving access to the corresponding triflate salts. Georg Thieme Verlag Stuttgart.