Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry.,Organic Letters

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Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-15 , DOI: 10.1021/acs.orglett.9b04450
Merlin Kleoff ₁ , Johannes Schwan ₁ , Lisa Boeser ₁ , Bence Hartmayer ₁ , Mathias Christmann ₁ , Biprajit Sarkar ₂ , Philipp Heretsch ₁

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A scalable access to functionalized ferrocenyl azides has been realized in flow. By halogen-lithium exchange of ferrocenyl halides and trapping with tosyl azide, a variety of functionalized ferrocenyl azides were obtained in high yields. To allow a scalable preparation of these potentially explosive compounds, a flow protocol was developed accelerating the reaction time to minutes and circumventing accumulation of potentially hazardous intermediates. The corresponding ferrocenyl amines were then prepared by a reliable reduction process.

中文翻译：

通过流动化学实现了功能化二茂铁叠氮化物和胺的可扩展合成。

在流动中已经实现了对官能化的二茂铁基叠氮化物的可扩展访问。通过卤素-锂交换二茂铁基卤化物并用甲苯磺酰基叠氮化物捕集，可以高收率获得各种官能化的二茂铁基叠氮化物。为使这些潜在爆炸性化合物的制备规模可扩展，开发了一种流动方案，可将反应时间缩短至数分钟，并避免潜在危险中间体的积累。然后通过可靠的还原方法制备相应的二茂铁胺。

更新日期：2020-01-15

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