A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process

IF 16.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Accounts of Chemical Research Pub Date : 2018-05-30 DOI:10.1002/hc.21418
Nader Ghaffari Khaligh
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引用次数: 3

Abstract

The preparation of aryl iodides in a telescopic reaction using tert-butyl nitrite as a diazotization reagent and a mixture of bis(trifluoromethane) sulfonamide and glacial acetic acid as a mild acidic agent in ethanol followed by iododediazoniation with tetraethylammonium iodide in water was investigated. The current method has other advantages such as minimized waste by avoiding solvent for the purification of products in diazotization step, simple experimental procedure, and good yield of the sterically hindered aryl amines, metal and strong acid-free waste and environmentally benign conditions. The noteworthy features of this study are the preparation of stable arenediazonium bis(trifluoromethylsulfonyl)imide salts that can be used with no significant loss activity after 1 week and bis(trifluoromethane)sulfonamide was recovered in high yields from reactions.

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使用稳定的阿二唑双(三氟甲基磺酰基)酰亚胺盐通过伸缩过程制备芳基碘化物的简单和可持续的方案
以亚硝酸叔丁酯为重氮化剂,双(三氟甲烷)磺胺和冰醋酸的混合物为弱酸性剂,在乙醇中用四乙基碘化铵进行碘脱氮化反应,研究了缩合反应制备芳基碘化物的工艺。该方法在重氮化过程中避免了溶剂的使用,减少了废弃物的产生,实验步骤简单,空间位阻芳胺产率高,无金属和强酸废弃物产率高,环境友好。本研究值得注意的特点是制备了稳定的芳氨重氮双(三氟甲基磺酰基)亚胺盐,可在1周后使用而无明显的活性损失,并通过反应高收率地回收了双(三氟甲烷)磺酰胺。
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来源期刊
Accounts of Chemical Research
Accounts of Chemical Research 化学-化学综合
CiteScore
31.40
自引率
1.10%
发文量
312
审稿时长
2 months
期刊介绍: Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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