87539-52-4

Upstream product

• 31599-50-5 4-methoxy(dichloroiodo)benzene 
• 696-62-8 para-iodoanisole 
• 16308-14-8 4-methoxy(diacetoxyiodo)benzene 

Downstream Products

• 23383-02-0 Dimedon-(4-methoxy-phenyl)-iodonium-betain 
• 16825-74-4 4-iodyl-anisole 
• 126550-93-4 <(hydroxy)(tosyloxy)iodo>-p-methoxybenzene 
• 696-62-8 para-iodoanisole 

Relevant academic research and scientific papers

CO2-activated NaClO-5H2O enabled smooth oxygen transfer to iodoarene: A highly practical synthesis of iodosylarene

A safe, rapid, and environmentally friendly synthesis of iodosylarene (ArIO) has been developed using NaClO under a carbon dioxide (CO2) atmosphere. Exposure of iodoarene to NaClO-5H2O in acetonitrile under CO2 (1 atm) resulted in the clean formation of ArIO within 10 minutes in high yield. The absence of a base in this method enables the direct use of in-situ-generated iodosylarene not only for a variety of oxidative transformations (synthesis of sulfilimine, pentavalent bismuth, benzyne adduct, etc.), but also for the synthesis of iodonium ylide and imino-λ3-iodane in one pot.

Fluorocyclization of N-Propargyl Carboxamides by λ3-Iodane Catalysts with Coordinating Substituents

Aiming at the enhanced catalytic activity of fluoro-λ3-iodane generated from iodoarene precatalyst with Selectfluor and HF?pyridine, this study focused on the λ3-iodanes bearing coordinating substituents. Compared to 4-iodoanisole as a precatalyst of our previous method, N-methyl-2-iodobenzamide or 2-iodobenzamide worked well in the fluorocyclization of N-propargyl carboxamides to oxazoles. Control experiments suggest the equilibrium mixture of iodane-amine complexes and cyclic iodane fluorides would be involved in the present catalysis. (Figure presented.).

SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN

Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.

Oxidase catalysis via aerobically generated hypervalent iodine intermediates

The development of sustainable oxidation chemistry demands strategies to harness O'2 as a terminal oxidant. Oxidase catalysis, in which O'2 serves as a chemical oxidant without necessitating incorporation of oxygen into reaction products, would allow diverse substrate functionalization chemistry to be coupled to O'2 reduction. Direct O'2 utilization suffers from intrinsic challenges imposed by the triplet ground state of O'2 and the disparate electron inventories of four-electron O'2 reduction and two-electron substrate oxidation. Here, we generate hypervalent iodine reagents - a broadly useful class of selective two-electron oxidants - from O'2. This is achieved by intercepting reactive intermediates of aldehyde autoxidation to aerobically generate hypervalent iodine reagents for a broad array of substrate oxidation reactions. The use of aryl iodides as mediators of aerobic oxidation underpins an oxidase catalysis platform that couples substrate oxidation directly to O'2 reduction. We anticipate that aerobically generated hypervalent iodine reagents will expand the scope of aerobic oxidation chemistry in chemical synthesis.

Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors

Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to produce functionalized [18F]fluoroarenes, regardless of the electronic nature of the arenes. This method was also applied to the production of radiolabeling synthons for use as aromatic 18F-labeled building blocks.

Metal-Free O-Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes

The metal-free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly-polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important key to this approach, and the introduction of the trimethoxybenzene auxiliary enables both the smooth salt formations and the selective aryl transfer events during the couplings. (Figure presented.).

NMR study on the structure and stability of 4-substituted aromatic iodosyl compounds

Two 4-substituted aromatic iodosyl compounds were investigated with regard to their solubility, stability and chromatographic behaviour. 1-Iodosyl-4-methoxy- and 1-iodosyl-4-nitro-benzene are soluble in methanol and provide acceptable 1H and s

Capture of Electron-Deficient Species with Aryl Halides. New Syntheses of Hypervalent Iodonium Ylides

We have demonstrated the aryl iodide capture of β-diketocarbenes, generated from the diazo compound by using rhodium(II) acetate, under very mild conditions.This is a useful general preparative method for iodonium ylides under non-hydroxylic conditions.The termal, catalytic, and photochemical decompositions of various azides in the presence of aryl iodides were carried out.With highly reactive nitrenes, intramolecular rearrangement takes precedence over capture.In the case of p-tuloenesulfonyl azide, thermolysis in the presence of aryl iodides requires conditions under which the iminoiodane is itself decomposed.The capture of oxene by iodobenzene is discussed.The application of these capture processes is discussed as a synthetic route to hypervalent ylides as well as on the basis of mechanism.

173.Ru-Catalyzed Oxidations with Iodosylbenzene Derivatives. Substituent Effects on Selectivity in Oxidation of Sulfides and Alcohols

Oxidation of sulfides witth PhIO/RuCl2(PPh3) leads to sulfones.Electronwithdrawing substituents in the aromatic ring of PhIO reduce the reactivity and improves selectivity of the system.Thus, with m-iodosylbenzoic acid sulfides are converted to sulfoxide.Under the same conditions aliphatic primary alcohols are transformed to aldehydes with m-iodosylbenzoic acid, while PhIO affords carboxylic acids.