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Upstream product

• 108-86-1 bromobenzene 
• 1493-13-6 trifluorormethanesulfonic acid 
• 4028-63-1 iodomesitylene 
• 589-87-7 1,4-bromoiodobenzene 
• 108-67-8 1,3,5-trimethyl-benzene 

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• 623-00-7 4-bromobenzenecarbonitrile 
• 253668-84-7 2-(4-bromophenyl)-1-methyl-1H-pyrrole 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 15224-36-9 thiophosphoric acid S-(4-bromophenyl) ester O,O'-diethyl ester 
• 1430342-22-5 2-(4-bromophenyl)-3-hydroxy-1-phenylpropan-1-one 
• 1383933-50-3 (3aS,8aR)-1-benzyl-3a-(4-bromophenyl)-8-methyl-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-2(1H)-one 
• 22421-88-1 4-bromobenzyl phenyl ketone 

Relevant academic research and scientific papers

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.

Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?

An anodic oxidation enabled synthesis of hypervalent iodine(III) reagents from aryl iodides is demonstrated. Under mild electrochemical conditions, a range of aryliodine(III) reagents including iodosylarenes, (difunctionaliodo)arenes, benziodoxoles and diaryliodonium salts can be efficiently synthesized and derivatized in good to excellent yields with high selectivity. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner avoiding the use of expensive or hazardous chemical oxidants.

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.

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.

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).

Copper-Catalyzed N-Arylation of Nitroenamines with Diaryliodonium Salts

A novel synthetic methodology was developed for the N-arylation of nitroenamine derivatives utilizing diaryliodonium triflates and copper(I) chloride as a catalyst. The procedure enables the easy aryl transfer from the hypervalent species under mild catalytic conditions with unusual heteroatom preference and high efficiency.

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.

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone

A straightforward synthesis of diaryliodonium salts is achieved by using Oxone as the stoichiometric oxidant. Slow addition is the key to obtaining good yields and purities of the reaction products, which are highly useful reagents in many different areas of organic synthesis.

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.