Iodomesitylene-Catalyzed Oxidative Cleavage of Carbon−Carbon Double and Triple Bonds Using m-Chloroperbenzoic Acid as a Terminal Oxidant

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• 作者：Kazunori Miyamoto ; Yoshihisa Sei ; Kentaro Yamaguchi ; Masahito Ochiai
• 刊名：Journal of the American Chemical Society
• 出版年：2009
• 出版时间：February 4, 2009
• 年：2009
• 卷：131
• 期：4
• 页码：1382-1383
• 全文大小：131K
• 年卷期：v.131,no.4(February 4, 2009)
• ISSN：1520-5126

文摘

Transition metal-catalyzed oxidative cleavage of carbon−carbon multiple bonds has emerged as a powerful tool in organic synthesis. High-valent oxometals, mostly of Ru, Os, Mn, Mo, W, and Re, were used catalytically as reactive oxygen transfer agents to the multiple bonds. Reported here for the first time are the organocatalytic versions of the oxidative cleavage reactions. Our method involves use of iodomesitylene as an effective organocatalyst, which generates an active aryl(hydroxy)-λ³-iodane 5 in situ, and m-chloroperbenzoic acid (m-CPBA) as a terminal oxidant under metal-free conditions. Cyclic and acyclic olefins as well as aliphatic and aromatic alkynes were smoothly cleaved to carboxylic acids under the organocatalytic conditions.