A highly chemoselective oxidation of alcohols to carbonyl products with iodosobenzene diacetate mediated by chromium(III)(salen) complexes:: Synthetic and mechanistic aspects

被引：68

作者：

Adam, W ^{[1
]}

Hajra, S ^{[1
]}

Herderich, M ^{[1
]}

Saha-Möller, CR ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem & Lebensmittel Chem, D-97074 Wurzburg, Germany

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol000142y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic oxidation of the allylic alcohols 1d-n with iodosobenzene diacetate, mediated by the [Cr-III(salen)]X complex, affords the respective enones in excellent chemoselectivity for Cl- as counterion [complex A(Cl)], while for the counterions TfO- [complex A(TfO)] and PF6- [complex A(PF6)] nearly equal amounts of enone and epoxide are observed. This counterion-dependent oxidation of allylic alcohols by Cr-III(salen) complexes is rationalized in terms of Lewis acid catalysis by the complex A(CI) and redox catalysis for A(TfO) and A(PF6).

引用

页码：2773 / 2776

页数：4

共 22 条

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