Synthesis of cyclobutane-fused chromanones via gold-mediated photocatalysis
This journal is © The Royal Society of Chemistry..
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:15 |
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| Enthalten in: |
Chemical science - 15(2024), 12 vom: 20. März, Seite 4571-4580 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Voloshkin, Vladislav A [VerfasserIn] |
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Date Revised 23.03.2024 published: Electronic-eCollection Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d3sc06675d |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a This journal is © The Royal Society of Chemistry. | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Villa, Marco |e verfasserin |4 aut | |
| 700 | 1 | |a Martynova, Ekaterina A |e verfasserin |4 aut | |
| 700 | 1 | |a Beliš, Marek |e verfasserin |4 aut | |
| 700 | 1 | |a Van Hecke, Kristof |e verfasserin |4 aut | |
| 700 | 1 | |a Ceroni, Paola |e verfasserin |4 aut | |
| 700 | 1 | |a Nolan, Steven P |e verfasserin |4 aut | |
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