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Controlling Photooxygenation with a Bifunctional Quinine‐BODIPY Catalyst: towards Asymmetric Hydroxylation of β‐Dicarbonyl Compounds
Author(s) -
Fischer Jérôme,
Mele Lucas,
SerierBrault Hélène,
Nun Pierrick,
Coeffard Vincent
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900984
Subject(s) - photooxygenation , photosensitizer , singlet oxygen , chemistry , bifunctional , bodipy , photochemistry , moiety , hydroxylation , catalysis , rose bengal , substrate (aquarium) , combinatorial chemistry , oxygen , organic chemistry , fluorescence , physics , oceanography , quantum mechanics , enzyme , geology
We report herein a new catalytic strategy towards asymmetric photooxygenation of β‐dicarbonyl compounds. Our method is based on the synthesis of a bifunctional photosensitizer composed of a quinine organocatalyst grafted to an iodo‐BODIPY framework capable of generating singlet oxygen. The quinine moiety serves both to interact with the substrate for promoting photooxygenation and to deactivate singlet oxygen in the absence of substrate. The bifunctional photosensitizer prepared was subsequently applied in the asymmetric oxygenation of a series of β‐dicarbonyl compounds under green light irradiation. Control experiments and kinetic analyses were carried out to shed the light on the mechanism.