1483-73-4

Usage

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

Upstream product

• 71-43-2 benzene 
• 932-72-9 (Dichloroiodo)benzene 
• 300669-23-2 triphenyl-iodan 
• 591-50-4 iodobenzene 
• 2217-79-0 diphenyliodonium iodide 
• 16668-99-8 bis(phenyl)iodonium trifluoroacetate 
• 591-51-5 phenyllithium 

Downstream Products

• 1709-51-9 N,N-diphenylbenzenesulfonamide 
• 4703-19-9 N,N-diphenyl-p-toluenesulfonamide 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 2243-42-7 2-phenoxybenzoic acid 
• 599-62-2 N-methyl-N-phenyltoluenesulfonamide 
• 58377-40-5 tert-butyl N-hydroxy-N-phenylcarbamate 
• 722-56-5 diphenyliodonium nitrate 
• 15171-63-8 N-phenoxy-1-benzyloxyformamide 
• 6092-74-6 N-benzoyloxycarbonylphenylhydroxylamine 
• 88312-86-1 6-phenyl-6H-dibenzo<1,2>thiazin 5,5-dioxide 
• 81614-78-0 5-Nitro-4-phenoxy-indan 
• 119-61-9 benzophenone 
• 92-52-4 biphenyl 

Relevant academic research and scientific papers

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.).

One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone-sulfuric acid

A facile synthesis of diaryliodonium salts utilizing Oxone as versatile and cheap oxidant has been developed. This method shows wide applicability and can be used for the preparation of iodonium salts containing electron-donating or electron-withdrawing groups in good yields. In addition, this procedure can be applied to the preparation of symmetric iodonium salts directly from arenes via a one-pot iodination-oxidation sequence.

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.

Halogen exchange via a halogenation of diaryliodonium salts with cuprous halide

An efficient halogenation reaction has been developed with diaryliodonium salts and cuprous halides. Various diaryliodonium salts 1 could perform the reaction with readily available CuBr or CuCl in CH3CN at 80°C, assembling bromoarenes or chloroarenes in up to 92% yields. This provides us a method for the transformation from iodoarenes to other haloarenes.

Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts

An efficient arylation of carboxylic acids with diaryliodonium salts has been developed, giving aryl esters in high yields within short reaction times for both aromatic and aliphatic substrates. The transition-metal-free conditions are compatible with a range of functional groups, and good chemoselectivity is observed with unsymmetric diaryliodonium salts. Furthermore, steric hindrance in the ortho positions is well tolerated both in the carboxylic acid and in the diaryliodonium salt, yielding aryl esters that cannot be obtained via other esterification protocols.

Facile syntheses of symmetrical diaryliodonium salts from various arenes, with sodium metaperiodate as the coupling reagent in acidic media

An easy, inexpensive, safe, and effective preparative procedure to obtain symmetrical diaryliodonium bromides (in 17-88% crude yields) from various arenes is presented in this paper. A novel method for the in situ preparation of iodosyl sulfate (Chretien's reagent) is given. Eleven exemplary crude diaryliodonium bromides were readily oxidatively metathesized with 40% aqueous tetrafluoroboric acid and 30% aqueous hydrogen peroxide (in boiling acetone, used both as a solvent and 'halogen scavenger') to give pure diaryliodonium tetrafluoroborates in 15-85% yields. Georg Thieme Verlag Stuttgart.

One-pot preparations of diaryliodonium bromides from iodoarenes and arenes, with sodium perborate as the oxidant

This paper reports a one-pot synthesis of the title bromides from both activated and deactivated iodoarenes which are first oxidized with anhydrous NaBO3·H2O/Ac2O/conc.H2SO 4 liquid mixtures, then coupled in situ with benzene and activated arenes and, finally, precipitated out with a KBr solution; this method is easy, cheap, safe and fairly effective.

Synthesis and characterization of 32 polybrominated diphenyl ethers

Polybrominated diphenyl ethers (PBDEs) are widely used as additive flame retardants in, for example, textiles, computers, television sets, and other electrical appliances. present also in humans. The environmental levels of the PBDEs are, however, still in general lower than those of polychlorinated biphenyls (PCBs). However, while the levels of PCBs generally are decreasing, those of the PBDEs are increasing in, for example, human milk. In the present study 32 individual PBDE congeners were synthesized and characterized. Physicochemical parameters including melting points and UV, 1H NMR, and mass spectra are reported Twenty-nine monobrominated to heptabrominated diphenyl ethers were synthesized by the couping between four diphenyliodonium salts and nine phenolates. One tetrabromodiphenyl ether and two hexabromodiphenyl ethers were synthesized by bromination of two different PBDEs. Twenty-one of the PBDEs and two of the iodonium salts, 2,2′,4,4′-tetrabromodiphenyliodonium chloride and 3,3′,4,4′-tatrabromodiphenyliodonium chloride, are to the authors' knowledge described for the first time. These synthesized reference compounds will aid in the identification and quantification of PBDEs present in environmental samples and will allow further assessment of PBDE toxicity.

Oxidative Anion Metatheses in Diaryliodonium Iodides and Chlorides

Oxidative anion metatheses in the crude title iodides and chlorides produced the corresponding pure hydrogensulfates, nitrates, tetrafluoroborates, triflates, tosylates, as well as bromides and chlorides (only from the iodides) in 54-86% yields. These procedures are easier and shorter than earlier methods. By using modified oxidative metatheses in the title iodides (in the presence of HBr or HCl) it was possible either to isolate, or to detect only, the intermediate dihaloiodates(I). [Ar2I]+[IX2]- (X = Br or Cl). A complex Ph2I+Cl- -1/2I2 was also obtained in 56% yield. Tetraethylammonium iodide was similarly converted into pure tetrafluoroborate or dibromoiodate(I) in 75 and 76% yields, respectively.

A short-cut synthesis of diaryliodonium bromides followed by oxidative anion metatheses

This paper reports a one-pot synthesis of the title bromides (in 20-88% crude yields) from iodoarenes oxidized with the CrO3/AcOH/Ac2O/H2SO4 liquid mixture, then coupled in situ with arenes and, finally, precipitated out with a KBr solution. Similarly, diaryliodonium perchlorates and iodides are obtained in 40-89% crude yields. Oxidative anion metatheses in the crude title bromides produce the respective pure diaryliodonium tetrafluoroborates, tosylates, trifluoroacetates, hydrosulfates, nitrates, and chlorides in 57-80% yields. These new preparative procedures are easier and shorter than many earlier methods.