Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 25, Issue 8, Pages 1943-1949Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.1c00187
Keywords
cascade; photochemistry; visible light; flow; Diels-Alder; rearrangement
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Funding
- EPSRC [EP/P013341/1, EP/S018050/1]
- Royal Society (University Research Fellowship)
- EPSRC [EP/P013341/1] Funding Source: UKRI
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This study demonstrates a rare example of a photo/thermal daisy-chained process, with the first visible-light-mediated excited state coupled with thermal cascade reaction conducted as a fully continuous process. The synthetic utility of flow chemistry is further showcased by the isolation of a reactive intermediate at quantities not possible under batch conditions.
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.
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