An Efficient and Regioselective Direct Aromatic Iodination Using Iodine and Nitrogen Dioxide

Regioselective iodination of arenes in ionic liquids mediated by SelectfluorTM reagent F-TEDA-BF4

“…The solvent was evaporated and the crude reaction mixtures were analyzed by NMR. 6 ]. To the ionic liquid (1.5 ml) containing I 2 (115 mg, 0.3 mmol) and F-TEDA-BF 4 (160 mg, 0.3 mmol) durene (120 mg, 0.6 mmol) and mesitylene (108 mg, 0.6 mmol) were added under argon.…”

“…3 The direct introduction of iodine into aromatic molecules is the most used methodology although the addition of activating agents is necessary, owing to the low electrophilicity of I 2 . Several methods using iodonium donating agents have therefore been developed, such as iodine-tetrabutylammonium peroxydisulfate, 4 BuLi-CF 3 CH 2 I, 5 iodinenitrogen dioxide, 6 iodine-F-TEDA-BF 4 , 7 iodine-iodine pentoxide, 8 iodine monochloride, 9 NIS-CF 3 SO 3 H, 10 iodine-mercury salts, 11 and NaOCl-NaI. 12 Most of these methods require toxic reagents or solvents and the reactions often occur with a low regioselectivity giving, besides the mono-iodo adducts, mixtures of poly-iodination products.…”

“…Herein we report an efficient method for the iodination of representative aromatic rings using iodine and 1-(chloromethyl) The present study was therefore undertaken to determine the efficacy of this iodinating system in an ionic liquid and to obtain, from comparison with molecular solvents, further information about the properties of these new reaction media. 6 ] was used as solvent, after the extraction of the reaction product, washing with water gave a pure ionic liquid (NMR) which may be re-used at least twice without significant modification in yield and selectivity. A number of different aromatic substrates was subjected to the iodination reaction to test the generality of this method, and the results are reported in Table 1.…”

Novel electrophilic aromatic iodine substitution of some naphtholic Schiff bases

“…Iodination of aromatic compounds was carried out by using molecular iodine together with Lewis acid or a strong oxidizing agent such as Ag 2 SO 4 , NaIO 4 , HIO 4 , NaOCl, liquid SO 3 , iodic acid, 3 nitric acid and sulfuric acid, 4 sulfur trioxide and hydrogen peroxide. [5][6][7][8][9] Recently, direct iodination methods have been reported using various iodinium donating reagents, such as iodine/Na 2 NaOCl-NaI, 12 bis(pyridineiodonium(I)tetrafluoroborate-CF 3 SO 3 H, 13 iodine silver sulfate, 14 NIS-CF 3 SO 3 H, 2 iodine-mercury salts, 15 iodine monochloride, 16 mercury(II)-oxide-iodine, 17 bis(symcollidine)iodine(I)hexafluorophosphate, 18 iodine-di-iodine pentoxide, 19 NIS (N-iodosuccinimide), 20 iodine-nitrogendioxide, 21 iodine-F-TEDA-BF 4,22 iodine-iodic acid, 23 n-BuLi-CF 3 CH 2 I, 24 NH 4 I-oxone, 25 ICl. 26 However, most of these methods require a high reaction temperature and long reaction times, 20 work in low yields, 27 involve toxic heavy metals, involve harsh conditions, and generate costly or complex and hazardous waste.…”

Regioselective iodination of hydroxylated aromatic ketones

“…In recent years, direct iodination methods have been intensively developed using iodinium donating systems, such as iodine nitrogen dioxide, 2 iodine-F-TEDA-[1-chloromethyl-4-fluoro- 14 Iodination of resorcinol derivatives and hydroxy chromones has been carried out using iodine and sodium hydroxide, 15 potassium iodide and potassium iodate 16 in acetic acid medium. However, most of these methods involve hazardous or toxic reagents.…”