利用碘代苯获得半稳定和非稳定重氮化合物

IF 2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Laurent Vinet, Emmanuelle M. D. Allouche, Vanessa Kairouz, André B. Charette
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引用次数: 0

摘要

连续流化学已成为合成重氮试剂等有毒和易爆中间体的首选方法,因为它们可以按需生成并随时使用,无需处理危险材料。这种内在安全性的提高使得在日常合成中使用这些试剂变得更加可行。在此,我们介绍一种连续流、无金属、易用的半稳定和非稳定重氮试剂制备方法。所描述的使用填料床柱与碘苯进行连续流氧化肼的范围包括二氯甲烷溶液中的 13 种半稳定重氮试剂和 13 种非稳定重氮试剂,同时只产生 1 个当量的水和碘苯作为副产品。这些原本难以获得的化合物可在原位或反应器出口处进一步反应,生成酯和醚,收率从良好到极佳(47-96%)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Access semi-stabilized and unstabilized diazo compounds using iodosylbenzene

Access semi-stabilized and unstabilized diazo compounds using iodosylbenzene

Continuous flow chemistry has become the method of choice for the synthesis of toxic and explosive intermediates such as diazo reagents because they can be generated on demand and readily used, eliminating the need to handle hazardous materials. This inherent increase in safety makes it more feasible to use these reagents in day-to-day synthesis. Herein, we describe a continuous flow, metal-free, easy-to-use method for the preparation of semi-stabilized and unstabilized diazo reagents. The scope of the described continuous flow oxidation of hydrazones using a packed bed column with iodosylbenzene includes 13 semi-stabilized and 13 unstabilized diazo reagents in solution in dichloromethane while producing only 1 equivalent of water and iodobenzene as by-products. These otherwise difficult to access compounds are further reacted either in situ or at the reactor outlet to yield esters and ethers in good to excellent yields (47–96%).

Graphical Abstract

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来源期刊
Journal of Flow Chemistry
Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
6.40
自引率
3.70%
发文量
29
审稿时长
>12 weeks
期刊介绍: The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.
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