N-hydroxyphthalimide/cobalt(II) catalyzed low temperature benzylic oxidation using molecular oxygen

被引：142

作者：

Wentzel, BB

Donners, MPJ

Alsters, PL

Feiters, MC

Nolte, RJM

机构：

[1] Univ Nijmegen, NSR Ctr, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands

[2] DSM Res, LS, CC, NL-6160 MD Geleen, Netherlands

来源：

TETRAHEDRON | 2000年 / 56卷 / 39期

关键词：

oxidation; catalysis; N-imides; cobalt;

D O I：

10.1016/S0040-4020(00)00679-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of(substituted) aryl glyoxylates is formed in good to excellent yield under very mild conditions by direct oxidation of the corresponding arylacetic esters or mandelic acid esters with molecular oxygen and N-hydroxyphthalimide/cobalt(II) acetate as catalyst. Heteroaromatic analogs are more difficult to oxidize with this system. The effect of substitution in the aromatic ring of N-hydroxyphthalimide on the oxidation of ethylbenzene has been studied. Electron withdrawing substituents accelerate the oxidation of ethylbenzene and promote the formation of acetophenone. Electron donating substituents lead to decreased rates of oxidation and enhance the selectivity for 1-phenylethanol. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：7797 / 7803

页数：7

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