66003-76-7

Usage

Uses

Used in Research Applications:
DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE is used as a research chemical for studying various chemical reactions and processes. Its unique properties make it a valuable tool in scientific research.
Used in Organic Synthesis:
DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE is used as a reagent for phenylation in organic synthesis. It aids in the formation of carbon-carbon bonds, which is crucial in the synthesis of various organic compounds.
Used in Photochemistry:
DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE is used as a cationic photoinitiator and photoacid generator in photochemistry. It initiates the polymerization process when exposed to light, making it useful in the production of polymers and other materials.

InChI:InChI=1/C12H10I.CHF3O3S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;2-1(3,4)8(5,6)7/h1-10H;(H,5,6,7)/q+1;/p-1

Upstream product

• 960-16-7 tributylphenylstannane 
• 141339-50-6 di(cyano)iodonium triflate 
• 1493-13-6 trifluorormethanesulfonic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 71-43-2 benzene 
• 536-80-1 iodosylbenzene 
• 2217-79-0 diphenyliodonium iodide 
• 1483-73-4 diphenyliodonium bromide 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 2926-30-9 sodium triflate 
• 1483-72-3 diphenyliodonium chloride 

Downstream Products

• 591-50-4 iodobenzene 
• 92-52-4 biphenyl 
• 2051-60-7 2-chloro-1,1'-biphenyl 
• 1591-31-7 4-iodo-biphenyl 
• 2113-51-1 2-iodobiphenyl 
• 20442-79-9 3-iodo-1,1'-biphenyl 
• 100-66-3 methoxybenzene 
• 103-84-4 Acetanilid 
• 71-43-2 benzene 
• 143521-46-4 1-phenyl-1-benzothiophenium trifluoromethanesulfonate 
• 3857-04-3 [18F]fluorobenzene 
• 84600-74-8 (77Br)bromobenzene 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 13740-67-5 2,2-diphenyl-1-indanone 

Relevant academic research and scientific papers

An efficient ligand exchange reaction of β-(trifyloxy)vinyliodonium triflates with aryllithium reagents leading to diaryliodonium triflates

Reaction of β-[[(trifluoromethylsulfonyl)oxy]vinyl](phenyl)-iodonium triflates with aryllithiums gave (aryl)(phenyl)iodonium triflates selectively. This reaction indicates that ligand exchange reaction takes place efficiently at iodine atom and provides another approach to unsymmetrical diaryliodonium salts.

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.

Scalable electrochemical synthesis of diaryliodonium salts

Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN-HFIP-TfOH without any added electrolyte salts. This atom efficient process does not require chemical oxidants and generates no chemical waste. More than 30 cyclic and acyclic diaryliodonium salts with different substitution patterns were prepared in very good to excellent yields. The reaction was scaled-up to 10 mmol scale giving more than four grams of dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (>95%) in less than three hours. The solvent mixture of the large-scale experiment was recovered (>97%) and recycled several times without significant reduction in yield.

Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts

Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

N1- and N3-Arylations of Hydantoins Employing Diaryliodonium Salts via Copper(I) Catalysis at Room Temperature

Copper(I)-catalyzed N-arylation (both N1- and N3-) of hydantoins with diaryliodonium salts as aryl partners at room temperature is reported. The transformation allows diverse scopes on both hydantoins and diaryliodonium salts deliver

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thio-/Selenocyanates

A straightforward protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition of aryl thio-/selenocyanates with donor-acceptor cyclopropanes (DACs) in the presence of SnCl4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3-cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)-cycloaddition reactions.

Direct Copper-Catalyzed C-3 Arylation of Diphenylphosphine Oxide Indoles

We have developed a simple and effective method for the C-3 arylation of phosphorus-containing indole compounds in the presence of CuI under mild conditions. This reaction provides a reliable method for the modification of ligands.

Palladium Catalyzed Regioselective Cyclization of Arylcarboxylic Acids via Radical Intermediates with Diaryliodonium Salts

Palladium-catalyzed C2-arylation/intramolecular acylation with arylcarboxylic acids was developed by using diaryliodonium salts. The protocol has the advantage of good step-economy by two chemical bonds formation in one pot.

Benzanthrone derivative and preparation method thereof and application thereof in functional pigments

The invention discloses a benzanthrone derivative and a preparation method thereof. The general formula is shown as a formula I or IV, formula I or IV, R1, R2, R3 is independently selected from hydrogen, halogen, an ester group, an acyl group, a branched-chain or straight-chain C1-C20 alkyl group, a straight-chain or branched-chain C1-C20 alkoxy group, a branched-chain or straight-chain perfluoroC1-C20 alkyl group, a branched-chain or straight-chain perfluoroC1-C20 alkoxy group, a substituted or unsubstituted C4-C40 aryl group, and a substituted or unsubstituted C4-C40 heteroaryl group. The benzanthrone derivative with a novel structure provided by the invention is simple in preparation method, non-toxic and harmless, has yellow fluorescence, can be used as a potential organic functional material, and is an important dye intermediate.