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m-Iodosylbenzoic Acid as a Convenient Recyclable Hypervalent Iodine Oxidant for the Synthesis of alpha-Iodo Ketones by Oxidative Iodination of Ketones

  作者 YUSUBOV MEHMAN S; YUSUBOVA ROSA Y; FUNK TATYANA V; CHI KIWHAN; KIRSCHNING ANDREAS; ZHDANKIN VIKTOR V  
  选自 期刊  Synthesis;  卷期  2010年-21;  页码  3681-3685  
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[摘要]A convenient procedure for the preparation of alpha-iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and beta-dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective alpha-iodo-substituted carbonyl compounds in excellent yields. The final products of iodination are conveniently separated from byproducts by simple treatment with anionic exchange resin Amberlite IRA 900 HCO3- and are isolated with good purity after evaporation of the solvent. The reduced form of the hypervalent iodine oxidant, m-iodobenzoic acid, can be recovered in 91-95% yield from the Amberlite resin by treatment with aqueous hydrochloric acid followed by extraction with ethyl acetate.

 
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