Diphenyldiselenide-Catalyzed Selective Oxidation of Activated Alcohols with tert-Butyl Hydroperoxide: New Mechanistic Insights

被引：32

作者：

van der Toorn, John C. ^{[1
,2
]}

Kemperman, Gerjan ^{[2
]}

Sheldon, Roger A. ^{[1
]}

Arends, Isabel W. C. E. ^{[1
]}

机构：

[1] Delft Univ Technol, Lab Biocatalysis & Org Chem, NL-2628 BL Delft, Netherlands

[2] Schering Plough Corp, Dept Proc Chem, NL-5342 CC Oss, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 08期

关键词：

AQUEOUS HYDROGEN-PEROXIDE; CARBONYL-COMPOUNDS; ALDEHYDES; KETONES; ACIDS;

D O I：

10.1021/jo900059y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Diselenides are known precatalysts for catalytic oxidations. The use of these widely available compounds as catalysts for the oxidation of alcohols was investigated, still leaving many mechanistic questions to be answered. By using a range of analytical techniques, we found evidence for the unexpected involvement of seleninic anhydride in the catalytic mechanism. The activation time of the diselenide and its influence on the oxidation reaction itself was also investigated. On the basis of these findings, an improved protocol for the selective oxidation of activated alcohols was devised resulting in significantly decreased catalyst loadings (< 1%).

引用

页码：3085 / 3089

页数：5

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