197245-87-7

Usage

Uses

Used in Organic Synthesis:
(3-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate is used as a reagent for the preparation of functionalized unsymmetrical diaryliodonium salts. These salts are valuable intermediates in organic synthesis, enabling the creation of a wide range of complex organic molecules with potential applications in various fields.
Used in Photoredox Catalysis:
In the field of photoredox catalysis, (3-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate is employed as a reagent for the arylation of arenes and heteroarenes. This process is crucial for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials. The use of photoredox catalysis allows for mild reaction conditions and enhanced selectivity, making it an attractive method for the synthesis of complex organic molecules.

Upstream product

• 108-67-8 1,3,5-trimethyl-benzene 
• 1493-13-6 trifluorormethanesulfonic acid 
• 19169-97-2 m-(diacetoxyiodo)toluene 
• 625-95-6 3-Iodotoluene 
• 108-88-3 toluene 

Downstream Products

• 1276111-42-2 (S)-2-(m-tolyl)-1-octanol 
• 34403-03-7 1-phenyl-2-(meta-tolyl)ethanone 
• 59960-39-3 N-(3-methylphenyl)-α-methyl-benzeneacetamide 
• 26977-45-7 N-(m-tolyl)-1H-indole-3-carboxamide 
• 15286-13-2 diethyl (m-tolyl)phosphonate 
• 1874-39-1 2-(3-methylphenyl)-5-phenyl-1,3,4-oxadiazole 
• 1566616-98-5 1,3-dimethyl-3-(3-methylbenzyl)indolin-2-one 
• 912762-89-1 1-methyl-2-(3-methylphenyl)-1H-pyrrole 

Relevant academic research and scientific papers

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.

Catalyst-Free Arylation of Tertiary Phosphines with Diaryliodonium Salts Enabled by Visible Light

The visible-light-induced arylation of tertiary phosphines with aryl(mesityl)iodonium triflates to produce the quaternary phosphonium salts occurs under mild, metal, and catalyst-free conditions. Photo-excited EDA complexes between diaryliodonium salts an

N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines

Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility of isolated N-aryl-DABCO salts is demonstrated for the preparation of flibanserin.

A Modular Flow Design for the meta-Selective C?H Arylation of Anilines

Described herein is an effective and practical modular flow design for the meta-selective C?H arylation of anilines. The design consists of four continuous-flow modules (i.e., diaryliodonium salt synthesis, meta-selective C?H arylation, inline copper extraction, and aniline deprotection) which can be operated either individually or consecutively to provide direct access to meta-arylated anilines. With a total residence time of 1 hour, the desired product could be obtained in high yield and excellent purity without the need for column chromatography, and the residual copper content meets the standards for parenterally administered pharmaceutical substances.

Flow Synthesis of Diaryliodonium Triflates

A safe and scalable synthesis of diaryliodonium triflates was achieved using a practical continuous-flow design. A wide array of electron-rich to electron-deficient arenes could readily be transformed to their respective diaryliodonium salts on a gram scale, with residence times varying from 2 to 60 s (44 examples).

A Modular Synthesis of 4-Aminoquinolines and [1,3] N-to-C Rearrangement to Quinolin-4-ylmethanesulfonamides

A copper-catalyzed regiocontrolled three-component reaction afforded diversified 4-aminoquinolines using nitriles, diaryliodoniums, and ynamides. The C7-substituted regioisomers were formed regioselectively when meta-substituted phenyliodonium salts were used. [1,3] N-to-C rearrangement of the products to quinolin-4-ylmethanesulfonamides and simultaneous deprotection of benzyl and sulfonamide group were newly developed. Finally, antimalarial CK-2-68 was successfully prepared.

Copper-catalyzed oxidative ring closure of ortho-cyanoanilides with hypervalent iodonium salts: Arylation-ring closure approach to iminobenzoxazines

A novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho-cyanoanilides and diaryliodonium triflates via an oxidative arylation-cyclization path. The reaction is supposed to involve the formation of highly active aryl-copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2-dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2-16 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.

Palladium-catalyzed P(O)R2 directed C-H arylation to synthesize electron-rich polyaromatic monophosphorus ligands

Palladium-catalyzed arylation of (diisopropylphosphoryl)biphenyl skeleton derivatives by the P(O)R2 directed C-H functionalization was reported. The related products were obtained in high regioselectivity and good functional group tolerance was observed. This reaction provided a new and efficient pathway for the synthesis of polyaromatic monophosphorus ligands. The Royal Society of Chemistry.

LCopper-catalyzed diarylation of activated alkenes with diaryliodonium salts

Cu(OTf)2-catalyzed diarylation of activated alkenes by using diaryliodonium(III) salts has been developed. With this method, arylated oxindoles can be easily accessed in good yields. Insights into the mechanism of copper-catalyzed arylations are discussed, and the findings are expected to help increase the level of understanding of catalytic arylations with diaryliodonium salts. Georg Thieme Verlag Stuttgart. New York.