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Updated: Jul 20, 2026
09:54
Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
[Development of environmentally benign oxidations using hypervalent iodine (III) reagents]
1Graduate School of Pharmaceutical Sciences, Osaka University, Suita City, Japan. td1203@phs.osaka-u.ac.jp
Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan
|September 2, 2006
Summary
Researchers developed new recyclable hypervalent iodine (III) reagents for efficient and environmentally friendly oxidations. These novel compounds demonstrate high reactivity and can be easily recovered and reused, enabling green chemistry applications.
Area of Science:
- Organic Chemistry
- Green Chemistry
Context:
- Hypervalent iodine (III) reagents are widely used in organic synthesis for various oxidation reactions.
- Conventional reagents often generate stoichiometric waste and can be difficult to recycle.
- Development of recyclable and environmentally benign oxidation catalysts is a key goal in sustainable chemistry.
Purpose:
- To synthesize and characterize novel, non-polymer-supported, recyclable hypervalent iodine (III) reagents.
- To evaluate the efficiency and scope of these new reagents in various oxidative transformations.
- To demonstrate the recyclability and reusability of the synthesized reagents in environmentally benign conditions, including aqueous media.
Summary:
- A novel class of recyclable hypervalent iodine (III) reagents, based on a tetrakis(phenyl)adamantane core (3a-c), has been synthesized.
- These reagents exhibit high reactivity in oxidative transformations, comparable to conventional reagents like phenyliodine (III) diacetate (PIDA) and superior to existing polymer-supported reagents.
- The tetraiodide intermediate is quantitatively recovered and reoxidized, enabling efficient recycling. Mild and clean oxidation of alcohols in water and facile aldehyde synthesis using a dual recycling strategy with TEMPO were achieved.
Impact:
- Provides highly efficient and recyclable hypervalent iodine (III) reagents for greener organic synthesis.
- Enables environmentally benign oxidation reactions in various organic solvents and water.
- Facilitates sustainable synthesis of aldehydes from primary alcohols through a dual recycling strategy.
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