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Fischer, J., Mele, L., Serier-Brault, H., Nun, P. & Coeffard, V. (2019) Controlling Photooxygenation with a Bifunctional Quinine-BODIPY Catalyst: towards Asymmetric Hydroxylation of beta-Dicarbonyl Compounds. Eur. J. Org. Chem. 2019 6352–6358.
Added by: Richard Baschera (2019-11-22 13:17:49) Last edited by: Richard Baschera (2019-11-22 13:20:08) |
| Type de référence: Article DOI: 10.1002/ejoc.201900984 Numéro d'identification (ISBN etc.): 1434-193X Clé BibTeX: Fischer2019 Voir tous les détails bibliographiques  |
Catégories: MIOPS Mots-clés: 2+2 photocycloaddition reactions, aerobic oxidation, asymmetric catalysis, enantioselective alpha-hydroxylation, energy transfer, furans, keto-esters, mechanistic insights, molecular-oxygen, one-pot synthesis, photooxidation, photoredox catalysis, singlet oxygen, singlet oxygen, Synthetic methods Créateurs: Coeffard, Fischer, Mele, Nun, Serier-Brault Collection: Eur. J. Org. Chem. |
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We report herein a new catalytic strategy towards asymmetric photooxygenation of beta-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 beta-dicarbonyl compounds under green light irradiation. Control experiments and kinetic analyses were carried out to shed the light on the mechanism.
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