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Aromatic Iodination: Iodine and NaIO4 or NaIO3

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Lego:
Simple and regioselective oxyiodination of aromatic compounds with ammonium iodide and Oxone®
K.V.V. Krishna Mohan, N. Narender, and S.J. Kulkarni
Tet. Lett., 2004, 45, 8015-8018
DOI:10.1016/j.tetlet.2004.09.010


Abstract: A simple method for the iodination of aromatic compounds using NH4I as the iodine source and Oxone® as the oxidant is described.



General procedure for the iodination of aromatic compounds: Oxone® (2.2 mmol) was added to a well-stirred solution of NH4I (2.2 mmol) and substrate (2.0 mmol) in methanol (10 mL) and the reaction mixture was allowed to stir at room temperature. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was filtered and solvent evaporated under reduced pressure. The products were purified by column chromatography over silica gel (finer than 200 mesh) with 5–30% ethyl acetate in hexane as eluent. All the structures of the products were confirmed by NMR and mass spectra.

java:
Note:This has been inserted here from Post 459094 (java: "Re: Novel easy preparations of Iodobenzene.....", Novel Discourse) to compliment this thread

Novel Easy Preparations of Some Aromatic Iodine(I, III, and V) Reagents, Widely Applied in Modern Organic Synthesis *

Lech Skulski

Molecules 8, 45-52,2003

http://www.mdpi.org/molecules/papers/80100045.pdf


Abstract:... We report our novel (or considerably improved) methods for the synthesis of aromatic iodides, (dichloroiodo)arenes, (diacetoxyiodo)arenes, [bis(trifluoroacetoxy)-iodo]arenes, iodylarenes and diaryliodonium salts, as well as some facile, oxidative anion
metatheses in crude diaryliodonium or tetraalkylammonium halides and, for comparison,potassium halides. All our formerly published papers were discussed and explained in our review ÒOrganic Iodine(I, III, and V) Chemistry: 10 Years of Development at the Medical University of Warsaw, PolandÓ (1990-2000) [1].

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