徳島大学 教育・研究者情報データベース(EDB)

1. 徳島大学.大学院ヘルスバイオサイエンス研究部.創薬資源科学部門.機能分子創製学講座(2004年4月1日〜)

1. 宮本 和範

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   貢献度	任意
   学籍番号	推奨

2. 落合 正仁

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(英) Organocatalytic Oxidative Cleavage of Carbon-Carbon Double Bonds

(日) 有機触媒による酸化的炭素ー炭素二重結合切断反応

(英) Oxidative cleavage of carbon-carbon double bonds to carbonyl compounds is an essential operation in organic synthesis. Ozonolysis is generally accepted as the standard method for this direct transformation. However, its utility is often limited by safety concerns. Use of high-valent oxometals such as RuO4, OsO4, and MeReO3 in combination with a number of oxygen donors as stoichiometric oxidants is suitable for the oxidative catalytic cleavage of olefins, but they are expensive and/or toxic. Therefore, the development of a safe and environmentally friendly procedure for the cleavage of carbon-carbon double bonds is highly desirable. In this review, we report a safe, environment-friendly, and heavy metal-free ozonolysis of olefins, which involves activated iodosylbenzene monomers, hydroxy-λ3-iodanes, as active species. Organocatalytic version of the oxidative cleavage of olefins that involves in situ generation of hypervalent aryl-λ3-iodanes as effective organocatalysts and the use of <I>m</I>-chloroperbenzoic acid as a stoichiometric terminal oxidant under metal-free conditions is described. Cyclic and acyclic olefins as well as aliphatic and aromatic alkynes were cleaved to carboxylic acids under the organocatalytic conditions.

1. オレフィン(olefin)
2. アルキン(alkyne)
3. (英) oxidative cleavage
4. 有機分子触媒(organocatalysts)
5. (英) m-CPBA
6. (英) hypervalent iodane
7. ヨウ素(iodine)
8. 臭素(bromine)