Dimethylformamide, dimethylacetamide and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes

被引：57

作者：

Ahmad, Simon M.

Braddock, D. Christopher ^{[1
]}

Cansell, Gemma

Hermitage, Stephen A.

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] GlaxoSmithKline Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

electrophilic bromination; alkenes; catalysis;

D O I：

10.1016/j.tetlet.2006.12.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dimethylformamide, dimethylacetamide and tetramethylguanidine were found to act as increasingly active catalysts for the bromolactonisation of gamma,delta- and delta,epsilon-unsaturated carboxylic acids with N-bromosuccinimide. The catalysts are readily removed in the work-up by washing with water to provide the pure bromolactone products without the need for column chromatography. Catalysis of the intermolecular bromoacetoxylation of alkenes with acetic acid and NBS by TMG was also demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：915 / 918

页数：4

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