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Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process

机译:使用苯胺作为掩蔽的交叉偶联伙伴:伸缩三步流重氮化,碘化二重氮化,交叉偶联工艺的设计

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摘要

The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow diazotization/iododediazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki-Miyaura and Sonogashira cross-coupled products.
机译:通过使用伸缩的三反应器流动重氮化/碘化重氮化/交叉偶联工艺,可以将市售苯胺转化为联芳基和联芳基乙炔产品。使用专门设计的连续流动装置(由内部创建的定制软件控制),将在桑德梅尔序列中通过除气产生的分段流动流恢复到反应溶液的连续塔中。然后将所得的芳基碘化物与进料到最终反应器中的交叉偶联溶液流合并。该系统被证明是通用的,因为可以快速进行重氮化/碘化重氮化序列的修饰以考虑任何底物特异性(例如,溶解性问题),从而导致Suzuki-Miyaura和Sonogashira交叉偶联产物的底物范围很广。

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