Iodobenzene-catalyzed α-acetoxylation of ketones.: In situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid
Iodobenzene-catalyzed α-acetoxylation of ketones.: In situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid
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DOI：
10.1021/ja0542800
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发表时间：
2005-09-07
影响因子：
15
通讯作者：
Miyamoto, K
中科院分区：
文献类型：
--
作者：
Ochiai, M;Takeuchi, Y;Miyamoto, K
Reported here for the first time is the iodobenzene-catalyzed α-oxidation of ketones, in which diacyloxy(phenyl)-λ3-iodanes generated in situ act as real oxidants of ketones andm-chloroperbenzoic acid serves as a terminal oxidant. Oxidation of a ketone withm-chloroperbenzoic acid in acetic acid in the presence of a catalytic amount of iodobenzene, BF3·Et2O, and water at room temperature under argon affords an α-acetoxy ketone in good yield.p-Methyl- andp-chloroiodobenzene also serve as efficient catalysts in this direct oxidation. We found that when the reaction was carried out in the absence of a catalytic amount of iodobenzene, Baeyer−Villiger oxidation of a ketone took place. It is noted that use of water and BF3·Et2O is crucial to the success of this α-acetoxylation.
