Iodobenzene-catalyzed α-acetoxylation of ketones.: In situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid

被引：336

作者：

Ochiai, M ^{[1
]}

Takeuchi, Y ^{[1
]}

Katayama, T ^{[1
]}

Sueda, T ^{[1
]}

Miyamoto, K ^{[1
]}

机构：

[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 35期

关键词：

D O I：

10.1021/ja0542800

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 and m-chloroperbenzoic acid serves as a terminal oxidant. Oxidation of a ketone with m-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- and p-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. Copyright © 2005 American Chemical Society.

引用

页码：12244 / 12245

页数：2

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