Multimodal Carbon Monoxide Photorelease from Flavonoids

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Authors

RAMUNDO Andrea HURTOVÁ Martina BOŽEK Igor Kacper OSIFOVÁ Zuzana RUSSO Marina NGOY Bokolombe Pitchou KŘEN Vladimír KLÁN Petr

Year of publication 2024
Type Article in Periodical
Magazine / Source Organic Letters
MU Faculty or unit

Faculty of Science

Citation
Web https://pubs.acs.org/doi/10.1021/acs.orglett.3c04141
Doi http://dx.doi.org/10.1021/acs.orglett.3c04141
Keywords PHOTOSENSITIZED OXYGENATION; DISSOCIATION-CONSTANTS; PHOTOINDUCED REACTIONS; PROTON-TRANSFER; SINGLET OXYGEN; 3-HYDROXYFLAVONES; PHOTOOXYGENATION; PHOTOCHEMISTRY; SPECTROSCOPY; MODEL
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Description Photooxygenation of flavonoids leads to the release of carbon monoxide (CO). Our structure-photoreactivity study, employing several structurally different flavonoids, including their C-13-labeled analogs, revealed that CO can be produced via two completely orthogonal pathways, depending on their hydroxy group substitution pattern and the reaction conditions. While photooxygenation of the enol 3-OH group has previously been established as the CO liberation channel, we show that the catechol-type hydroxy groups of ring B can predominantly participate in photodecarbonylation.
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