Synthesis of cyclobutane-fused chromanones via gold-mediated photocatalysis.

Autor:	Voloshkin VA; Department of Chemistry, Centre for Sustainable Chemistry, Ghent University Krijgslaan 281, S-3 9000 Ghent Belgium Steven.Nolan@ugent.be., Villa M; Department of Chemistry 'Giacomo Ciamician', Center for Chemical Catalysis-C3, University of Bologna Via Selmi, 2 40126 Bologna Italy Paola.Ceroni@unibo.it., Martynova EA; Department of Chemistry, Centre for Sustainable Chemistry, Ghent University Krijgslaan 281, S-3 9000 Ghent Belgium Steven.Nolan@ugent.be., Beliš M; Department of Chemistry, Centre for Sustainable Chemistry, Ghent University Krijgslaan 281, S-3 9000 Ghent Belgium Steven.Nolan@ugent.be., Van Hecke K; Department of Chemistry, Centre for Sustainable Chemistry, Ghent University Krijgslaan 281, S-3 9000 Ghent Belgium Steven.Nolan@ugent.be., Ceroni P; Department of Chemistry 'Giacomo Ciamician', Center for Chemical Catalysis-C3, University of Bologna Via Selmi, 2 40126 Bologna Italy Paola.Ceroni@unibo.it., Nolan SP; Department of Chemistry, Centre for Sustainable Chemistry, Ghent University Krijgslaan 281, S-3 9000 Ghent Belgium Steven.Nolan@ugent.be.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2024 Feb 21; Vol. 15 (12), pp. 4571-4580. Date of Electronic Publication: 2024 Feb 21 (Print Publication: 2024).
DOI:	10.1039/d3sc06675d
Abstrakt:	Energy transfer (EnT) photocatalysis has emerged as a valuable tool for constructing complex organic scaffolds via [2 + 2]-cycloaddition reactions. Herein, we present the use of [Au(SIPr)(Cbz)] as a sensitizer for the [2 + 2]-cycloaddition of coumarins and unactivated alkenes. Widely used in EnT catalysis, iridium and organic sensitizers proved less efficient under the examined catalytic conditions. The developed protocol permits the synthesis of cyclobutane-fused chromanones from readily available starting materials. A wide range of alkenes and substituted coumarins, including naturally occurring compounds, were reacted under mild conditions leading to structurally complex products with good functional group tolerance. Mechanistic studies reveal a previously overlooked reaction pathway for energy transfer catalysis involving coumarins. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu