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Issue 8, 2009
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Aerobic oxidative iodination of ketones catalysed by sodium nitrite “on water” or in a micelle-based aqueous system

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Abstract

Selective and efficient aerobic oxidative iodination of ketones in aqueous media was achieved by using molecular iodine as the source of iodine atoms, air as the terminal oxidant, sodium nitrite (NaNO2) as the catalyst and H2SO4 as the activator of the overall catalytic process. The efficiency of the reaction, resulting in α-iodo ketones, was significantly improved in an aqueous solution of the anionic amphiphile sodium dodecyl sulfate (SDS), capable of self-assembly into micelle-based aggregates, thus forming a reactive micellar system. The regioselectivity of iodofunctionalization of aryl methyl ketones was regulated by the reaction medium used: in an aqueous micelle-based system the methyl group was iodinated, while in anhydrous MeCN aryl iodides were formed with high selectvity.

Graphical abstract: Aerobic oxidative iodination of ketones catalysed by sodium nitrite “on water” or in a micelle-based aqueous system

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Article information


Submitted
03 Feb 2009
Accepted
12 May 2009
First published
08 Jun 2009

Green Chem., 2009,11, 1262-1267
Article type
Paper

Aerobic oxidative iodination of ketones catalysed by sodium nitrite “on water” or in a micelle-based aqueous system

G. Stavber, J. Iskra, M. Zupan and S. Stavber, Green Chem., 2009, 11, 1262
DOI: 10.1039/B902230A

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