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首页> 外文期刊>Chemistry: A European journal >Magnesium Lewis Acid Assisted Oxidative Bromoetherification Involving Bromine Transfer from Alkyl Bromides with Aldehydes by Umpolung of Bromide
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Magnesium Lewis Acid Assisted Oxidative Bromoetherification Involving Bromine Transfer from Alkyl Bromides with Aldehydes by Umpolung of Bromide

机译：路易斯酸镁辅助氧化溴醚化反应，涉及溴化物的Umpolung从烷基溴化物与醛的溴转移

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摘要

An oxidative bromoetherification involving a bromine transfer from alkyl bromides upon reacting them with aldehydes in a Grignard reaction with a concurrent oxidation of bromide was developed to provide substituted tetrahydrofurans in high yields. This reaction, which proceeds through two types of bromine transfer, was promoted by the addition of a Bronsted acid. Mechanistic studies suggested that a magnesium Lewis acid activates hypobromate, which is generated in situ from the reaction of bromide and Oxone to improve the electrophilicity of the bromonium ion (Br+) for the oxidative bromoetherification of alkenyl alcohols. Furthermore, the magnesium Lewis acid catalyzed oxidative bromoetherification of an alkenyl alcohol proceeded to provide a cyclization product in 92% yield.
机译：已开发出一种氧化溴醚化方法，该方法涉及在烷基苯甲酸酯与格列尼亚德反应中与醛反应并同时进行溴化氧化的同时从烷基溴化物转移溴，以提供高收率的取代四氢呋喃。通过添加布朗斯台德酸促进了通过两种类型的溴转移进行的该反应。机理研究表明，路易斯酸镁活化了次溴酸盐，该次溴酸盐是由溴化物和Oxone反应原位生成的，以提高溴离子（Br +）的亲电子性，以实现烯醇的氧化性溴化醚化作用。此外，镁路易斯酸催化的链烯醇的氧化溴代醚化反应以92％的收率提供了环化产物。

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