Synthesis of iodoarenes

Name Reactions

Recent Literature

Deactivated arenes were mono- or diiodinated with strong electrophilic I⁺ reagents, which were prepared from NaIO₄ and either I₂ or KI in concentrated sulfuric acid, using either a ‘direct’ or an ‘inverse’ method of aromatic iodination to give mono- or diiodinated pure products in good yields.
L. Kraszkiewicz, M. Sosnowski, L. Skulski, Synthesis, 2006, 1195-1199.

A selective and efficient oxidative iodination of electron rich arenes was carried out with one equivalent of KI and two equivalents of 30% hydrogen peroxide in MeOH in the presence of strong acid.
J. Iskra, S. Stavber, M. Zupan, Synthesis, 2004, 1869-1873.

Various methoxy- or methyl-substituted aromatic compounds were regioselectively iodinated with N-iodosuccinimide and and a catalytic amount of trifluoroacetic acid with excellent yields under mild conditions and short reaction times.
A.-S. Castanet, F. Colobert, P.-E. Broutin, Tetrahedron Lett., 2002, 43, 5047-5048.

N-Halosuccinimides are efficiently activated in trifluoromethanesulfonic acid and BF₃-H₂O, allowing the halogenations of deactivated aromatics. BF₃-H₂O is more economic, easy to prepare, nonoxidizing, and offers sufficiently high acidity.
G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esteves, Q. Wang, G. Rasul, G. A. Olah, J. Am. Chem. Soc., 2004, 126, 15570-15776.

Eco-friendly laboratory procedures allow the oxidative iodination of various activated and deactivated arenes with molecular iodine, in the presence of UHP (percarbamide), a stable, strongly H-bonded, solid urea-hydrogen peroxide adduct as the oxidant.
P. Lulinski, A. Kryska, M. Sosnowski, L. Skulski, Synthesis, 2004, 441-445.

Benzene derivatives bearing at least one bulky alkyl group (i-Pr or t-Bu) were selectively and effectively iodinated using elemental iodine activated by Selectfluor. Up to three iodine atoms were progressively introduced at the most electron-rich and sterically less hindered position on the benzene ring.
S. Stavber, P. Kralj, M. Zupan, Synthesis, 2002, 1513-1518.

Convenient and simple, sequential diazotization-iodination of aromatic amines with NaNO₂/KI in the presence of a sulfonic acid based cation-exchange resin in water is an inexpensive, noncorrosive and eco-friendly synthetic route, that allows the preparation of various electron-rich and deficient iodoarenes in good yields.
V. D. Filimonov, N. I. Semenischeva, E. A. Krasnokutskaya, A. N. Tretyakov, H. Y. Hwang, K.-W. Chi, Synthesis, 2008, 185-187.

A convenient and general one-step preparation of aromatic and some heterocyclic iodides in good yields includes a sequential diazotization-iodination of aromatic amines with KI, NaNO₂, and p-TsOH in acetonitrile at room temperature.
E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis, 2007, 81-84.

Reaction of [ArN₂][BF₄] salts immobilized in [BMIM][PF₆] ionic liquid (IL) with TMSI and TMSN₃ represents an efficient method for the preparation of iodo- and azido-derivatives via dediazoniation. Using TMSBr, competing fluorodediazoniation (ArF formation) and hydrodediazoniation (ArH formation) were observed depending on the substituents on the benzenediazonium cation.
A. Hubbard, T. Okazaki, K. K. Laali, J. Org. Chem., 2008, 73, 316-319.

Kinetic vs thermodynamic deprotonation studies on secondary and tertiary sulfonamides using n-BuLi have been carried out. Application of the developed conditions allows the synthesis of diverse sulfonamide products (E=I). Subsequent Suzuki cross-coupling reactions of iodo derivatives furnish various biaryl sulfonamides.
S. L. MacNeil, O. B. Familoni, V. Snieckus, J. Org. Chem, 2001, 66, 3662-3670.

A mild palladium-catalyzed, regioselective chlorination, bromination, and iodination of arene C-H bonds using N-halosuccinimides as oxidants is described. These transformations can provide products that are complementary to those obtained via conventional electrophilic aromatic substitution reactions.
D. Kalyani, A. R. Dick, W. Q. Anani, M. S. Sanford, Org. Lett., 2006, 8, 2523-2526.

A mild and general copper(I)-catalyzed conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed. Various functional groups and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions.
A. Klapars, S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 14844-14845.

Aryl and heteroaryl boronic acids react with N-iodosuccinimide and N-bromosuccinimide to give the corresponding iodo- and bromo-arenes in good to excellent yields. The reaction is usually highly regioselective and yields only the ipso-substituted product.
C. Thiebes, G. K. Surya Prakash, N. A. Petasis, G. A. Olah, Synlett, 1998, 141-142.

J. Sedelmeier, C. Bolm, J. Org. Chem., 2005, 70, 6904-6906.

(Hetero)aryl-, alkenyl-, and selected alkyl-substituted acid chlorides can be efficiently coupled with N-Boc-protected propargylamine to produce ynones which are converted to 2-substituted N-Boc-4-iodopyrroles in a one-pot reaction. Upon addition of a further alkyne, another Sonogashira coupling can be carried out in a one-pot fashion.
E. Merkul, C. Boersch, W. Frank, T. J. J. Müller, Org. Lett., 2009, 11, 2269-2272.

A method for the regiospecific synthesis of 1,4,5-trisubstituted-1,2,3-triazole catalyzed by copper(I) iodide was developed. This is the first example of a regiospecific synthesis of 5-iodo-1,4-disubstituted-1,2,3-triazole, which can be further elaborated to a range of 1,4,5-trisubstituted-1,2,3-triazole derivatives
Y.-M. Wu, J. Deng, Y. L. Li, Q.-Y. Chen, Synthesis, 2005, 1314-1318.