Machine assisted reaction optimization: A self-optimizing reactor system for continuous-flow photochemical reactions

A methodology for the synthesis of oxetanes from benzophenone and furan derivatives is presented. UV-light irradiation in batch and flow systems allowed the [2 + 2] cycloaddition reaction to proceed and a broad range of oxetanes could be synthesized in manual and automated fashion. The identificatio...

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Published inTetrahedron Vol. 74; no. 25; pp. 3171 - 3175
Main Authors Poscharny, K., Fabry, D.C., Heddrich, S., Sugiono, E., Liauw, M.A., Rueping, M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.06.2018
Elsevier
Subjects
Chemistry
Chemistry, Organic
Flow chemistry
FTIR spectroscopy
Photocyclization
Physical Sciences
Science & Technology
Self-optimization
Self-optimization
Photocyclization
Flow chemistry
FTIR spectroscopy
SLUG FLOW
LIGHT
MICROFLOW PHOTOCHEMISTRY
MICROREACTOR
FURAN
STEREOSELECTIVITY
CHEMICAL-SYNTHESIS
MICROCAPILLARY REACTOR
PATERNO-BUCHI REACTION
PHOTOCYCLOADDITION REACTIONS
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Summary:A methodology for the synthesis of oxetanes from benzophenone and furan derivatives is presented. UV-light irradiation in batch and flow systems allowed the [2 + 2] cycloaddition reaction to proceed and a broad range of oxetanes could be synthesized in manual and automated fashion. The identification of high-yielding reaction parameters was achieved through a new self-optimizing photoreactor system. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.04.019