Photooxygenation reactions under flow conditions: An experimental and in-silico study

The photooxygenation reaction of a different set of olefins was investigated in LED flow reactor module from both experimental and in silico point of view. Initially, operating parameters potentially affecting the photoreaction efficiency, including the loading of the photosensitizer (methylene blue) (mol%), residence time and temperature were screened. The optimal conditions were then applied for the synthesis of 1,2-dioxetanes proving a straightforward and scalable approach to important chemiluminescent molecular probes for bioanalytical and diagnostic applications. Moreover, the scope of the reaction was tested for the oxidation of diverse alkenes under Schenck ene conditions providing synthetically useful allyl hydroperoxides. From this, a chemometric analysis was performed to propose a preliminary in silico model useful to both rationalize and predict the photooxygenation reaction outcome.