Iodomesitylene-catalyzed oxidative cleavage of carbon-carbon double and triple bonds using m-chloroperbenzoic acid as a terminal oxidant.
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)-lambda(3)-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.
Miyamoto
Kazunori
K
Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan.
Sei
Yoshihisa
Y
Yamaguchi
Kentaro
K
Ochiai
Masahito
M
D000475:Alkenes / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D002723:Chlorobenzoates / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction
D000475:Alkenes; D001555:Benzene Derivatives; D002723:Chlorobenzoates; D006847:Hydrocarbons, Iodinated; D016877:Oxidants; C539405:iodomesitylene; D002244:Carbon; C000433:3-chloroperbenzoic acid