Aromatic iodination with the I2-HgX2 combination

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

“…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.…”

Selective iodination of 2-acetyl-1-naphthol using iodine and iodic acid under solvent-free grinding technique

“…They are also important and the most reactive intermediates for various cross-coupling reactions and especially useful for formation of carbon-carbon and carbon-heteroatom bonds [4]. Recently the reagents reported for iodination of arenes include, iodine-nitrogen dioxide [5], iodine F-TEDA-[1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2,2,2] octane-bis-(tetrafluoroborate)] [6], bis-N-iodosuccinimide [7], trichloroisocyanuric acid-I2-Wet SiO2 [8], mercury(II)-oxide-iodine [9], iodine-monochloride [10], bis(pyridine)iodonium(I), tetrafluoroborate CF3SO3H [11], NIS-CF3SO3H [12], iodine silver sulfate [13], iodine-mercury salts [14] and NaOCl-NaI [15]. However, most of these methods suffer from major drawbacks such as use of harsh conditions, toxic heavy-metal catalysts, non-slectivity and longer reaction times.…”

Direct Green Iodination of Phenol over Solid Acids

“…Among the various reported methods we recall the use of molecular iodine with heavy metal salts (I 2 /HgX 2 , I 2 /HgO, I 2 /Ag 2 SO 4 , I 2 /Pb(OAc) 4 /HOAc) [11][12][13][14][15][16], molecular iodine with various oxidants (I 2 /KMnO 4 , I 2 /NaIO 3 , I 2 /NaIO 4 ) [17][18][19], or other systems employing less common reagents (I 2 /F-TEDA-BF 4 , ICl, I 2 /PhI(OAc) 2 , NIS, NaOCl-NaI) [20][21][22][23][24][25][26] in organic solvents. When the use of molecular iodine is concerned, formation of hydrogen iodide occurs thus causing proteolytic cleavage of particular sensitive compounds.…”