A photocatalyzed oxidation of functionalized cyclobutanones to access -lactones has been performed in acetonitrile at room temperature, using anthraquinone derivatives as catalysts in the presence of TFA. The best condition for the reaction was studied investigating a series of substituted antraquinones and irradiating the reaction at different wavelengths under O2 environment. The scope of the reaction was studied using both 2- and 3-substituted cyclobutanones, as well as enantiopure ketones obtain full preservation of its stereochemical identity after the oxidation. The process furnishes in most cases the desired compounds with high purity after simple filtration of the catalyst, reducing the production of solvents waste.

Low‐Impact Synthesis of γ‐Lactones through Photoinduced Baeyer‐Villiger Oxidation of Cyclic Ketones

Cabua, Maria Chiara
Primo
Methodology
;
Pilia, Luca
Visualization
;
Moi, Davide
Penultimo
Investigation
;
Secci, Francesco
Ultimo
Supervision
2024-01-01

Abstract

A photocatalyzed oxidation of functionalized cyclobutanones to access -lactones has been performed in acetonitrile at room temperature, using anthraquinone derivatives as catalysts in the presence of TFA. The best condition for the reaction was studied investigating a series of substituted antraquinones and irradiating the reaction at different wavelengths under O2 environment. The scope of the reaction was studied using both 2- and 3-substituted cyclobutanones, as well as enantiopure ketones obtain full preservation of its stereochemical identity after the oxidation. The process furnishes in most cases the desired compounds with high purity after simple filtration of the catalyst, reducing the production of solvents waste.
2024
Anthraquinones; Photo-oxidation; Cyclobutanone; gama-Lactone; Photocatalysis
File in questo prodotto:
File Dimensione Formato  
Eur J Org Chem - 2024 - Cabua - Low‐Impact Synthesis of ‐Lactones through Photoinduced Baeyer‐Villiger Oxidation of Cyclic.pdf

Solo gestori archivio

Tipologia: versione editoriale (VoR)
Dimensione 3.65 MB
Formato Adobe PDF
3.65 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
Eur_JOC_2024_accepted.pdf

embargo fino al 05/04/2025

Tipologia: versione post-print (AAM)
Dimensione 1.48 MB
Formato Adobe PDF
1.48 MB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11584/400563
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 1
  • ???jsp.display-item.citation.isi??? 1
social impact