Daisy-Chaining Photo- and Thermal Chemistry: Multistep Continuous Flow Synthesis of Visible-Light-Mediated Photochemistry with a High-Temperature Cascade Reaction,Organic Process Research & Development

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Daisy-Chaining Photo- and Thermal Chemistry: Multistep Continuous Flow Synthesis of Visible-Light-Mediated Photochemistry with a High-Temperature Cascade Reaction
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2021-07-19 , DOI: 10.1021/acs.oprd.1c00187
Luke D. Elliott ₁ , Kevin I. Booker-Milburn ₁ , Alastair J. J. Lennox ₁

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A highly efficient visible-light-mediated photochemical [2 + 2] cycloaddition is coupled with an atom economic thermal cascade reaction in a continuous flow process. By moving the photochemistry from ultraviolet (UV) to visible, it is made more energy-efficient and can be conducted with readily available equipment. The application of high-temperature flow chemistry to the thermal cascade step allows for safe and reliable scale-up with short reaction times. Thus, we demonstrate a rare example of a photo/thermal daisy-chained process and, specifically, the first visible-light-mediated excited state to the thermal cascade reaction as a fully continuous process (20 g/h). The synthetic utility of flow chemistry is further showcased by the isolation of a reactive intermediate at quantities not possible under batch conditions.

中文翻译：

菊花链光化学和热化学：可见光介导光化学的多步连续流动合成与高温级联反应

在连续流动过程中，高效的可见光介导的光化学 [2 + 2] 环加成与原子经济的热级联反应相结合。通过将光化学从紫外线 (UV) 转移到可见光，它变得更加节能，并且可以使用现成的设备进行。将高温流动化学应用于热级联步骤可以在较短的反应时间内实现安全可靠的放大。因此，我们展示了一个罕见的光/热菊花链过程的例子，特别是第一个可见光介导的激发态作为一个完全连续的过程 (20 g/h) 的热级联反应。流动化学的合成效用通过在批量条件下不可能的量分离反应性中间体而进一步展示。

更新日期：2021-08-20

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