117934-81-3

An environmentally benign CO2/glycol reversible acidic system was developed for the iron(iii)-catalyzed aerobic oxidative iodination of electron-rich aromatics without the need for any conventional acid additive or organic solvent. Notably, moderate to high isolated yields (up to 97%) of the aryl iodides were attained with comparable regioselectivity when ferric nitrate nonahydrate was used as the catalyst with molecular iodine under 1 MPa of CO2.

Reaction of aromatic compounds with bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4) in the presence of HBF4 or CF3SO3H in CH2Cl2 at room temperature furnishes monoiodo derivatives with excellent regioselectivity and yields.Use of either acid gives comparable results with activated aromatics, whereas CF3SO3H is much more effective in the iodination of deactivated aromatics.

A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.

A mild and practical method for the transition metal-free protodecarboxylation of aromatic acids using readily available and safe sodium persulfate as initiator was described. This environment-friendly decarboxylation approach was performed at 60 °C in ethanol and could easily scale up to the gram level with a good yield. In Particular, the tandem reactions of decarboxylation and halogenation were achieved by the addition of the corresponding halogenating reagents to the reaction system.

The invention discloses a method for synthesizing mono-aryl iodide or di-aryl iodide based on aromatic hydrocarbon carboxylic acid decarboxylic reaction. The method is characterized in that under a protective atmosphere, carrying out one-pot reaction on a

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

Selective monoiodination of aromatic compounds such as dimethoxybenzene has been successfully achieved with I+, which is generated by anodic oxidation of I2 in acetonitrile, using micromixing. The Royal Society of Chemistry 2006.

[figure: see text] Organotelluride 1 is a water-soluble catalyst for the oxidation of iodide with hydrogen peroxide in pH 6 phosphate buffer. In two-phase systems, organic substrates are efficiently iodinated using 0.8 mol % of catalyst. Water-soluble substrates are iodinated without an organic cosolvent.

To better understand, and in the extension mimic, the action of the three selenium-containing iodothyronine deiodinases, o,o'-diiodophenols were reacted under acidic conditions with sodium hydrogen telluride, benzenetellurol, sodium hydrogen selenide, or benzeneselenol and under basic conditions with the corresponding deprotonated reagents. Sodium hydrogen telluride was found to selectively remove one iodine from a variety of 4-substituted o,o'-diiodophenols, including a protected form of thyroxine (T4). Thus, it mimics the D1 variety of the iodothyronine deiodinases. Sodium telluride was a more reactive deiodinating agent toward o,o'-diiodophenols, often causing removal of both halogens. Benzenetellurol and sodium benzenetellurolate sometimes showed useful selectivity for monodeiodination. However, the products were often contaminated by small amounts of organotellurium compounds. Sodium hydrogen selenide, sodium selenide, benzeneselenol, and sodium benzeneselenolate were essentially unreactive toward o,o'-diiodophenols. To gain more insight into thyroxine inner-ring deiodination, substituted 2,6-diiodophenyl methyl ethers were treated with some of the chalcogen reagents. Reactivity and selectivity for monodeiodination varied considerably depending on the substituents attached to the aromatic nucleus. In general, it was possible to find reagents that could bring about the selective mono- or dideiodination of these substrates.

Treatment of various aromatic compounds with 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 1A and iodine gave the corresponding iodinated compounds in good yields. Similarly, chlorination and bromination proceeded effectively. As compared with other trivalent iodine compounds, the iodinane 1A showed the best reactivity as a halogenation reagent.

A convenient method for selective mono- and diiodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane is reported.

The reaction of aromatic ethers with benzyltrimethylammonium dichloroiodate(1-) in acetic acid in the presence of zinc chloride at room temperature gave iodo-substituted aromatic ethers in good yields.