Cascade Sequence of Photooxygenation–Epoxidation for the Flow Synthesis of Epoxy Alcohols

A photooxygenation–epoxidation cascade sequence converting alkenes to epoxy alcohols was developed and evaluated in batch and continuous-flow systems. In the batch system, the undesired interactions between the photooxygenation and epoxidation catalysts resulted in suboptimal yields, whereas the fin...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 89; no. 10; pp. 6960 - 6965
Main Authors Kim, Ji Eun, Son, Go Eun, Lim, Hyo Jin, Jang, Yea Seul, Song, Chan Ho, Park, Chan Pil
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.05.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
OXIDATIONS
METHYLENE-BLUE
SINGLET OXYGEN
DEGRADATION
CATALYST
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Summary:A photooxygenation–epoxidation cascade sequence converting alkenes to epoxy alcohols was developed and evaluated in batch and continuous-flow systems. In the batch system, the undesired interactions between the photooxygenation and epoxidation catalysts resulted in suboptimal yields, whereas the fine control of reaction parameters in the flow system allowed the allyl hydroperoxides produced through photooxygenation of alkenes to be rapidly converted to epoxy alcohols in yields of up to 93%. The developed procedure allows one to avoid an important synthetic bottleneck, works well where traditional batch synthesis fails, and can be scaled up to meet the needs of industrial production, thus presenting a valuable addition to the toolbox of practicing organic chemists.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00322