14353-88-9

Usage

Uses

Used in Chemical Synthesis:
[BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE is used as a reactant or reagent for the following applications:
1. Oxidation of organic iodides using oxone and trifluoroacetic acid: It serves as an effective oxidizing agent, facilitating the conversion of organic iodides to the desired products.
2. Base hydrolysis: The compound can be used to promote hydrolysis reactions under basic conditions, leading to the formation of the corresponding products.
3. Oxidative cross-coupling of arenes: It acts as a coupling agent, enabling the formation of biaryl compounds through an oxidative process.
4. Oxidation of phenolic compounds with organohypervalent iodine: The compound is utilized to oxidize phenolic compounds, leading to the formation of various products with organohypervalent iodine.
5. Aziridination of alkenes: It is employed as a reagent in the aziridination process, where alkenes are converted to aziridines.
6. Oxidation of organic compounds: The compound is used to oxidize a wide range of organic compounds, promoting the formation of oxidized products.
7. Oxidative fragmentation of α-amino acids or β-amino alcohols: It is used to selectively oxidize and fragment α-amino acids or β-amino alcohols, leading to the formation of specific products.
8. Oxidative biaryl coupling of thiophenes: The compound is employed as a reagent in the oxidative coupling of thiophenes to form biaryl compounds.

InChI:InChI=1/C10F11IO4/c11-1-2(12)4(14)6(5(15)3(1)13)22(25-7(23)9(16,17)18)26-8(24)10(19,20)21

Upstream product

• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 407-25-0 trifluoroacetic anhydride 
• 359-48-8 trifluoroacetyl peroxide 
• 76-05-1 trifluoroacetic acid 
• 14353-90-3 1,2,3,4,5-pentafluoro-6-iodosylbenzene 
• 1109-15-5 tris(pentafluorophenyl)borate 

Downstream Products

• 111873-60-0 C₇H₄F₅IO₄S 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 24973-39-5 pentafluoro(difluoroiodo)benzene 
• 14353-90-3 1,2,3,4,5-pentafluoro-6-iodosylbenzene 
• 76-05-1 trifluoroacetic acid 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 24973-40-8 pentafluorophenyliodine dinitrate 
• 75269-58-8 pentafluorophenyliodine dioxide 
• 64492-76-8 μ-oxobis(pentafluorophenyl)dinitratodiiodine(III) 
• 66966-42-5 2-phenyl-2-propen-1-yl trifluoroacetate 
• 1483-44-9 2-(trifluoromethyl)terephthalonitrile 
• 101066-87-9 4-iodo-2-(trifluoromethyl)benzonitrile 
• 161320-00-9 4-iodo-3-trifluoromethylbenzonitrile 
• 107317-58-8 4-bromo-3-trifluoromethylbenzoic acid methyl ester 

Relevant academic research and scientific papers

Simple direct synthesis of [bis(trifluoroacetoxy)iodo]arenes

A modified procedure for the direct synthesis of hypervalent [bis(trifluoroacetoxy)iodo]arenes is described. It avoids the use of hazardous reagents with the workup being only an aqueous extraction. Georg Thieme Verlag Stuttgart.

O-Insertion into Nonactivated C-H Bonds: The First Observation of O2 Cleavage by P-450 Enzyme Model in the Presence of a Thiolate Ligand

On reaction with 'O'-donors or O2, the synthetic P-450 analogue 2 undergoes O-insertion at a nonactivated C-H bond of the covalently bound substrate.The mechanism of O-insertion with O2 most likely involves homolytic cleavage of the O-O bond followed by O-insertion via radical recombination.

Alternative Strategies with Iodine: Fast Access to Previously Inaccessible Iodine(III) Compounds

Non-iodinated arenes can be easily and selectively converted into (diacetoxyiodo)arenes in a single step under mild conditions by using iodine triacetates as reagents. The oxidative step is decoupled from the synthesis of hypervalent iodine(III) reagents, which can now be prepared conveniently in a one-pot synthesis for subsequent reactions without prior purification. The chemistry of iodine triacetates was also expanded to heteroatom ligand exchanges to form novel inorganic hypervalent iodine compounds.

Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt-Derived Amphiphiles

Two sets of 19 amphiphiles derived from diaryliodonium salt in the form of 4-methylbenzenesulfonate salts and trifluoromethanesulfonate salts were synthesized in good yields through the oxidation of 17 different aryl iodides using oxone (potassium peroxymonosulfate) as the oxidation agent in Route I and meta-chloroperoxybenzoic acid as the oxidation agent in Routes II and III, followed by Friedel–Crafts reaction with (2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene to obtain the target compounds (1–19). Their structures were characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, and high-resolution mass spectrometry studies. Their surface activities were evaluated on the basis of surface tension and critical micelle concentration measurements by the Wilhelmy plate method at 25 °C. With their good water solubility, diaryliodonium salts (1–19) have excellent short-term bactericidal efficacy against Bacillus cereus in the concentration of 600 ppm at 20 °C. After compounding 1 or 18 with the broad-spectrum but skin-irritating antibacterial agent Kathon CG (methylchloroisothiazolinone in combination with methylisothiazolinone) in the ratio of 1:1 by mass, both formulations maintained lethality rate of >90% after 48 h.

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.

Development of Imino-λ3-iodanes with Improved Reactivity for Metal-Free [2+2+1] Cycloaddition-Type Reactions

Aiming at the enhancement of electrophilicity of imino-λ3-iodanes, we have developed (tosylimino)pentafluorophenyl-λ3-iodane, which shows superior reactivity compared to the commonly used (tosylimino)phenyl-λ3-iodane in the [2+2+1]-type synthesis of imidazoles. (Figure presented.).

Fluorine-containing diaryliodonium salt and application thereof

The invention relates to fluorine-containing diaryliodonium salt as well as a preparation method and an application thereof. The fluorine-containing diaryliodonium salt has a structure represented as a formula I and is taken as an arylation reagent. The fluorine-containing diaryliodonium salt has the advantages that the preparation is easy, when the fluorine-containing diaryliodonium salt is applied to an arylation reaction, the arylation reaction condition is relatively mild, the selectivity of an arylation product is good and the like; in the formula I shown in the specification, R1 represents an aromatic ring group or a heteroaromatic ring group or represents a substituted aromatic ring group or a substituted heteroaromatic ring group, and Y represents a univalent organic or inorganic acid radical anion.

A general and convenient preparation of [Bis(trifluoroacetoxy)iodo] perfluoroalkanes and [Bis(trifluoroacetoxy)iodo] arenes by oxidation of organic iodides using Oxone and trifluoroacetic acid

"Chemical Equation Presented" [Bis(trifiuoroacetoxy)iodo] perfiuoroalkanes CnF2n+1I(OC-OCF3)2 (n = 4, 6, 8, 10, 12) can be conveniently prepared by the oxidation of the corresponding perfluoroalkyl iodides with Oxone in trifluoroacetic acid at room temperature and subsequently converted to the stable [hydroxy(tosyloxy)-iodo] perfluoroalkanes, CnF2n+1I(OH)OTs, by treatment with p-toluenesulfonic acid. This general and convenient procedure has been further extended to the synthesis of various [bis(trifluoroacetoxy)iodo]arenes, ArI(OCOCF3)2.