Iodination Of Aromatic Compounds Research Articles

Palladium-Catalyzed C-H Iodination of Arenes by Means of Sulfinyl Directing Groups.

C-H iodination of aromatic compounds has been accomplished with the aid of sulfinyl directing groups under palladium catalysis. The reaction proceeds selectively at the peri-position of polycyclic aryl sulfoxides or at the ortho-position of phenyl sulfoxides. The iodination products can be further converted via iterative catalytic cross-coupling at the expense of the C-I and C-S bonds. Computational studies suggest that peri-C-H palladation would proceed via a non-directed pathway, wherein neither of the sulfur nor oxygen atom of the sulfinyl group coordinates to the palladium before and at the transition state.

Organic Synthesis of Iodinated Atorvastatin via Nucleophilic Substitution Reaction: Experimental and DFT Studies

Atorvastatin is an aromatic compound that acts selectively in the liver as an inhibitor of HMG-CoA reductase and cholesterol synthesis. The iodination of aromatic compounds has been widely applied for the preparation of potential pharmaceuticals and bioactive molecules. Herein, an iodinated atorvastatin was synthesized using chloramine-T (CAT) intermediate via an electrophilic substitution reaction. The obtained product was elucidated via elemental analysis, mass spectrometry and H-1-NMR techniques. A comparison of experimental H-1-NMR chemical shifts of the iodinated atorvastatin with the corresponding predicted ones obtained with GIAO method at the B3LYP/LanL2DZ confirmed the desired structure. Furthermore, the favourable electrophilic substitution site was confirmed by the Fukui indices calculations of the heavy atoms of the parent atorvastatin at DFT with the same level of theory.

Direct Iodination of Aromatic Compounds by Using Polymer-Supported Dichloroiodate as an Efficient Reagent under Mild Conditions

A new polymeric reagent was prepared by supporting dichloroiodate on poly (1,4-phenylene-2,5-pyridine dicarboxylamide). This polymeric reagent was used for the direct iodination of arenes under mild aprotic conditions.

Ultrasound-promoted iodination of pyrazoles in aqueous medium

Several pharmacological activities have been devoted to pyrazole containing molecules. In particular, 4-iodopyrazoles have been employed as key starting materials in cross-coupling chemistry and metal-iodine exchange reactions that focus on the synthesis of such biologically important compounds. Unfortunately, existing methods for the synthesis of 4-iodopyrazoles are not in agreement with the environmental requirements due to a series of drawbacks including the use of large excess of reagents, the generation of toxic waste and long reaction times. Recently, we developed a fast and mild reaction condition for the iodination of aromatic compounds using an I 2 /H 2 O 2 system water as a nonflammable and innocuous solvent and ultrasonic irradiation as energy source. In this work, we present the application of this methodology for the iodination of pyrazoles (Scheme). Initially, a series of pyrazoles were efficiently prepared starting from 1,3-dicarbonyl compounds and hydrazines under ultrasonic irradiation. Three examples from the pyrazoles were subjected to the iodination condition shown above. Iodopyrazoles were obtained in 63-65% yields.

Iodination of Activated Aromatic Compounds Using Nanostructure Solid Acid Catalyst

Nanoporous silica anchored with sulfonic acid groups effectively catalyzes the iodination of aromatic compounds. The reaction was performed in water using hydrogen peroxide as oxidant. The recyclability of catalyst in green media significantly contributes to the environmental friendliness of the procedure.

ChemInform Abstract: Efficient Iodination of Aromatic Compounds Using Potassium Ferrate Supported on Montmorillonite.

Abstract Potassium ferrate impregnated on montmorillonite is a mild, cheap, and non-toxic reagent for the iodination of phenols, including naphthol, aromatic amines, and heterocyclic substrates in fair to excellent yields by a simple isolation procedure.

Regioselective bromination and iodination of aromatic substrates promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane

Selective and efficient bromination and iodination of aromatic compounds by ammonium bromide and ammonium iodide, respectively, under promotion of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane have been explored. Mild reaction conditions, high selectivity and yield, and high reaction rate are some of the major advantages of this synthetic method.

A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid

This article describes simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product.

ChemInform Abstract: Direct Iodination of Aromatic Compounds with Iodine and Alumina- Supported Copper(II) Chloride or Sulfate.

The iodination of aromatic compounds (polymethylbenzenes, alkyl phenyl ethers, and polynuclear aromatic hydrocarbons) with iodine in combination with copper(II) chloride or sulfate supported on alumina proceeds well under mild conditions to selectively give monoiodinated compounds in high yields.

ChemInform Abstract: Iodination of Aromatic Compounds Using Potassium Iodide and Hydrogen Peroxide.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Mild and Efficient Iodination of Aromatic Compounds with Trichloroisocyanuric Acid/I_2/Wet SiO_2 System

Aromatic halogenated compounds have been used for over a century as important chemicals or intermediates in organic synthesis. Iodoarenes are valuable intermediates in the synthesis of a wide variety of organic compounds via reactions involving C-C bond formation by transition metals. They have many applications in pharmacology, medicine, and biochemistry. Since iodine is the least reactive halogen towards the electrophilic substitution, direct iodination of aromatic compounds with iodine is difficult. A large diversity of methods for synthesis of aromatic iodides have been reported. Some of the reported procedures need harsh conditions such as HNO3 /H2SO4 , HIO3 or HIO4 /H2SO4 , KMnO4 /H2SO4, CrO3 in acidic solution with I2 , vanadium salts/CF3SO3H at 100 ◦C,9 Pb(OAc)4 /HOAc. NIS/CF3SO3H has also been reported for direct iodination of highly deactivated aromatics. The other reported protocols are: I2 /HgX2 , ICl/Ag2SO4/H2SO4 , NIS/CF3CO2H , I2 /Ag2SO4 , I2 /F-TEDA-BF4 ,NIS/CH3CN , and(CH3)4 NICl2 . Our goal, in undertaking this line of work, was to overcome the limitations and drawbacks of the reported methods, which mentioned above, and also, to develop a high-yielding one-pot synthesis of iodoarenes using a novel combination of reagents. ∗Corresponding author

Iodination of Alkylbenzenes using Benzyltriphenylphosphonium Dichromate / I2 System

An efficient and rapid method have been found using benzyltriphenylphosphonium dichromate (PhCH2PPh3)2Cr2O7 as an oxidant along with molecular iodine for the iodination of aromatic compounds. Iodination of a wide variety of alkyl benzenes were done under dichloromethane solvent system and high yields of iodo products were obtained

Iodination of Aromatic Compounds Using Potassium Iodide and Hydrogen Peroxide

A simple, efficient, regioselective, and ecofriendly method for oxyiodination of aromatic compounds is presented. In this method, the electrophilic substitutions of iodine generated in situ from KI as an iodine source and hydrogen peroxide as an oxygen source have been employed without any catalyst/mineral acid for the first time.

Solvent‐Free Iodination of Arenes at Room Temperature.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Iodination of Aromatic Compounds under Mild and Solvent‐Free Conditions.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Iodination of Aromatic Compounds with Iodine and n -Butyl- triphenylphosphonium Peroxodisulfate

Iodine and n-butyltriphenylphosphonium peroxodisulfate can be successfully used for the iodination of some aromatic compounds in acetonitrile as solvent. The yields obtained are good to excellent.

Solvent-Free Iodination of Arenes at Room Temperature

Silica supported bismuth(III)nitrate pentahydrate [BNP-SiO 2 ] was prepared under simple co-grinding condition. The iodination of aromatic compounds using BNP-SiO 2 and molecular iodine under solvent-free conditions is described. The reaction occurred in the solid state at room temperature, yielding the corresponding mono-iodo derivative in good yields. However, less activated aromatics required longer reaction time with comparatively less vield.

ChemInform Abstract: Iodination of Aromatic Compounds by N‐Iodosuccinimide in Organic Solvents in the Presence of H2SO4.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Iodination of Aromatic Compounds with Iodine Monochloride in Aqueous Sulfuric Acid.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

2,4,6,8-Tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione as a mild and convenient reagent for iodination of aromatic compounds

2,4,6,8-Tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (tetraiodoglycoluril) is a convenient reagent for preparative iodination of benzene, alkylbenzenes, polycyclic hydrocarbons, aromatic amines, and phenol ethers in organic solvents under mild conditions.