Daisy-Chaining Photo- and Thermal Chemistry: Multi-Step Continuous Flow Synthesis of Visible-Light Mediated Photo-chemistry with a High Temperature Cascade Reaction

Alastair J J Lennox*, Luke D Elliott, Kevin I Booker-Milburn

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

Abstract

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 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 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.
Original languageEnglish
JournalOrganic Process Research & Development
Publication statusAccepted/In press - 12 Jul 2021

Keywords

  • cascade
  • photochemistry
  • visible light
  • flow
  • Diels-Alder
  • rearrangement

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