Selective oxidation of aromatic aldehydes to arenecarboxylic acids using ebselen-tert-butyl hydroperoxide catalytic system

被引：33

作者：

Wójtowicz, H ^{[1
]}

Brzaszcz, M ^{[1
]}

Kloc, K ^{[1
]}

Mlochowski, J ^{[1
]}

机构：

[1] Wroclaw Univ Technol, Inst Organ Chem Biochem & Biotechnol, PL-50370 Wroclaw, Poland

来源：

TETRAHEDRON | 2001年 / 57卷 / 48期

关键词：

aldehydes; tert-butyl hydroperoxide; carboxylic acids; ebselen; oxidation;

D O I：

10.1016/S0040-4020(01)00961-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been found that aromatic aldehydes with electron-withdrawing as well as electron-donating substituents are oxidized to arenecarboxylic acids using tert-butyl hydroperoxide in the presence of ebselen (2-phenylbenzisoselenazol-3(2H)-one) as a catalyst. The reaction is highly chemoselective and formation of phenols, being the products of competitive Baeyer-Villiger rearrangement, is marginal. It has been assumed that this rearrangement is inhibited by steric hindrance of the electron-deficient oxygen atom in the transient tetrahedral intermediate. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9743 / 9748

页数：6

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