Vanadium-catalyzed oxidative bromination promoted by Bronsted acid or Lewis acid

被引：49

作者：

Kikushima, Kotaro ^{[1
]}

Moriuchi, Toshiyuki ^{[1
]}

Hirao, Toshikazu ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2010年 / 66卷 / 34期

关键词：

Vanadium catalyst; Oxidative bromination; Molecular oxygen; Lewis acid; HYDROGEN-PEROXIDE; SYNTHETIC PROTOCOL; BROMIDE; ALKENES; MILD; HALOPEROXIDASES; HALOGENATION; COMPLEXES; OXYGEN; BROMOPEROXIDASE;

D O I：

10.1016/j.tet.2010.06.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidative bromination of arenes was induced by a vanadium catalyst in the presence of a bromide salt and a Brensted acid or a Lewis acid under molecular oxygen, which provides an eco-friendly bromination method as compared with a conventional bromination one with bromine. This catalytic reaction could be applied to the bromination of alkenes and alkynes to give the corresponding vic-bromides. Use of aluminum halide as a Lewis acid in place of a Brensted acid was demonstrated to provide a more practical protocol for the oxidative bromination. From ketones, alpha-bromination products were obtained. AlBr3 was found to serve as both a bromide source and a Lewis acid to induce the bromination smoothly. V-51 NMR experiment showed that this catalytic bromination is likely to depend on the redox cycle of a vanadium catalyst under molecular oxygen. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6906 / 6911

页数：6

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