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Updated: May 6, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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ディハロイオダレネス:フェニルアセテート誘導体のα,α-ジハロゲン化

Jason Tao1, Richard Tran, Graham K Murphy

  • 1Department of Chemistry, University of Waterloo , Waterloo, Ontario, Canada , N2L3G1.

Journal of the American Chemical Society
|October 25, 2013
PubMed
まとめ

研究者らは,高価ヨウ素反応剤を用いたα-カルボニル二酸化酸化のための新しい方法を開発した. この反応は,ダイアゾアセテート誘導体を,ジェム・ジクロライドやジェム・ジフローライドのようなジェム・ディ機能化された製品に効率的に変換します.

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
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Introduction
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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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