Organocatalytic Oxidative Cleavage of Carbon-Carbon Double Bonds
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- Miyamoto Kazunori
- Graduate School of Pharmaceutical Sciences, University of Tokushima
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- Ochiai Masahito
- Graduate School of Pharmaceutical Sciences, University of Tokushima
Bibliographic Information
- Other Title
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- 有機触媒による酸化的炭素‐炭素二重結合切断反応
- 有機触媒による酸化的炭素-炭素二重結合切断反応
- ユウキ ショクバイ ニ ヨル サンカテキ タンソ タンソ 2ジュウ ケツゴウ セツダン ハンノウ
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Description
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 m–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.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 68 (3), 228-237, 2010
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282680289882496
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- NII Article ID
- 10026868188
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- NII Book ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC3cXjt1yru70%3D
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 10612647
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed