Dimethylformamide, dimethylacetamide and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
Dimethylformamide, dimethylacetamide and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
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DOI：
10.1016/j.tetlet.2006.12.042
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发表时间：
2007-02-05
影响因子：
1.8
通讯作者：
Hermitage, Stephen A.
中科院分区：
文献类型：
--
作者：
Ahmad, Simon M.;Braddock, D. Christopher;Hermitage, Stephen A.
二甲基甲酰胺，二甲基乙酰胺和四甲基胍被发现作为越来越活跃的催化剂的γ，δ-和δ，ε-不饱和羧酸与N-溴代琥珀酰亚胺的溴内酯化。催化剂在后处理中通过用水洗涤容易地除去，以提供纯的溴内酯产物，而不需要柱色谱。TMG对烯烃与乙酸和NBS的分子间溴乙酰氧基化反应也有催化作用。(c)2006爱思唯尔有限公司保留所有权利。
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.