Iodination of Aromatic Compounds Using Potassium Iodide and Hydrogen Peroxide

Regioselective iodination of chlorinated aromatic compounds using silver salts

“…As mentioned above, the iodination of phenol ( 1a ) with a range of reagents, for example KI/H 2 O 2 /AcOH, 43 KI/KClO 3 /HCl, 44 CAN/I 2 , 28 NaBO 3 ·4H 2 O/I 2 in ionic liquids, 45 H 5 PV 2 Mo 10 O 40 polyoxometalate/I 2 , 46 ICl/DDQ/ferrocenium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate 47 or NIS/PTSA, 17 typically results in good yields and para selectivity; however, ortho iodination of 1a reportedly occurs with a number of silver salts and iodine, for example Ag 2 SO 4 /I 2 and AgNO 3 /I 2 in DCM. 48 In this study, conversion of 79% and 100% were observed for iodinations of 1a with AgSbF 6 /I 2 and AgBF 4 /I 2 , respectively, and the yields of 2a and 3a were poor (Table 3; entries 3-1 and 3-2).…”

“…31 Similarly, the direct iodination of aniline ( 1d ) with different reagents, for example KI/H 2 O 2 /AcOH, 43 KI/KClO 3 /HCl, 44 KI/KIO 3 /HCl, 49 CAN/I 2 , 28 NaBO 3 ·4H 2 O/I 2 in ionic liquids, 45 H 5 PV 2 Mo 10 O 40 polyoxometalate/I 2 , 46 ICl/DDQ/ferrocenium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate 47 or bis(sym-collidine)iodine(I) hexafluorophosphate, 41 yields 3d as the major product. The only reported selective synthesis of 2d (46% yield) by direct iodination of 1d employs Ag 2 SO 4 /I 2 in 1,2-ethanediol as iodinating reagent.…”

Chiral CNN Pincer Palladium(II) Complexes with 2-Aryl-6-(oxazolinyl)pyridine Ligands: Synthesis, Characterization, and Application to Enantioselective Allylation of Isatins and Suzuki–Miyaura Coupling Reaction

“…Solvents were dried with standard methods and freshly distilled prior to use if needed. 1-Iodo-2-methoxynaphthalene, 1-iodo-2-ethoxynaphthalene, and 1-iodo-2-benzyloxynaphthalene, arylboronic acid, and isatins were prepared according to the literature methods. All other chemicals were used as purchased.…”

Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions

“…Several reagents reported for iodination of aromatic compounds include iodine and 1,4-bis (triphenylphosphonium)-2-butene peroxodisulfate [3], iodine and pyridine/dioxane [4], AgNO 3 /I 2 [5], I 2 /NaBO 3 .4H 2 O in ionic liquid [6], I 2 /HIO 3, heat [7], I 2 /Pb(OAc) 4 [8], I 2 /CrO 3 [9], NaClO 2 /NaI/HCl [10], KI/K 2 FeO 4 in water [11], N-iodosuccinimide and catalytic trifluoroacetic acid [12], pyCl/CH 3 OH [13], KI/H 2 O 2 [14], KI/KIO 3 /H + [15], KClO 3 /KI/HCl [16], NCS/NaI [17] and iodine with H 2 O 2 and O 2 [18]. However, in spite of their potential utility, the practical application of most of these reagents suffers from disadvantages such as harsh reaction conditions, low regioselectivity, the use of expensive or less easily available reagents, long reaction times, low yields and tedious work-up.…”