Synthesis of cyclobutane-fused chromanones via gold-mediated photocatalysis
- Author
- Vladislav Voloshkin (UGent) , Marco Villa, Ekaterina Martynova, Marek Beliš (UGent) , Kristof Van Hecke (UGent) , Paola Ceroni and Steven Nolan (UGent)
- Organization
- Project
- Abstract
- 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.
- Keywords
- VISIBLE-LIGHT PHOTOCATALYSIS, LEWIS-ACID CATALYSIS, CROSS-PHOTOCYCLOADDITIONS, PHOTOCHEMICAL-REACTIONS, ORGANIC-PHOTOCHEMISTRY, COUMARIN, PHOTODIMERIZATION, DERIVATIVES, CYCLOADDITIONS, PHOTOCLEAVAGE
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01HZKVBM5GZA732SC031EE40JY
- MLA
- Voloshkin, Vladislav, et al. “Synthesis of Cyclobutane-Fused Chromanones via Gold-Mediated Photocatalysis.” CHEMICAL SCIENCE, vol. 15, no. 12, 2024, pp. 4571–80, doi:10.1039/d3sc06675d.
- APA
- Voloshkin, V., Villa, M., Martynova, E., Beliš, M., Van Hecke, K., Ceroni, P., & Nolan, S. (2024). Synthesis of cyclobutane-fused chromanones via gold-mediated photocatalysis. CHEMICAL SCIENCE, 15(12), 4571–4580. https://doi.org/10.1039/d3sc06675d
- Chicago author-date
- Voloshkin, Vladislav, Marco Villa, Ekaterina Martynova, Marek Beliš, Kristof Van Hecke, Paola Ceroni, and Steven Nolan. 2024. “Synthesis of Cyclobutane-Fused Chromanones via Gold-Mediated Photocatalysis.” CHEMICAL SCIENCE 15 (12): 4571–80. https://doi.org/10.1039/d3sc06675d.
- Chicago author-date (all authors)
- Voloshkin, Vladislav, Marco Villa, Ekaterina Martynova, Marek Beliš, Kristof Van Hecke, Paola Ceroni, and Steven Nolan. 2024. “Synthesis of Cyclobutane-Fused Chromanones via Gold-Mediated Photocatalysis.” CHEMICAL SCIENCE 15 (12): 4571–4580. doi:10.1039/d3sc06675d.
- Vancouver
- 1.Voloshkin V, Villa M, Martynova E, Beliš M, Van Hecke K, Ceroni P, et al. Synthesis of cyclobutane-fused chromanones via gold-mediated photocatalysis. CHEMICAL SCIENCE. 2024;15(12):4571–80.
- IEEE
- [1]V. Voloshkin et al., “Synthesis of cyclobutane-fused chromanones via gold-mediated photocatalysis,” CHEMICAL SCIENCE, vol. 15, no. 12, pp. 4571–4580, 2024.
@article{01HZKVBM5GZA732SC031EE40JY,
abstract = {{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.}},
author = {{Voloshkin, Vladislav and Villa, Marco and Martynova, Ekaterina and Beliš, Marek and Van Hecke, Kristof and Ceroni, Paola and Nolan, Steven}},
issn = {{2041-6520}},
journal = {{CHEMICAL SCIENCE}},
keywords = {{VISIBLE-LIGHT PHOTOCATALYSIS,LEWIS-ACID CATALYSIS,CROSS-PHOTOCYCLOADDITIONS,PHOTOCHEMICAL-REACTIONS,ORGANIC-PHOTOCHEMISTRY,COUMARIN,PHOTODIMERIZATION,DERIVATIVES,CYCLOADDITIONS,PHOTOCLEAVAGE}},
language = {{eng}},
number = {{12}},
pages = {{4571--4580}},
title = {{Synthesis of cyclobutane-fused chromanones via gold-mediated photocatalysis}},
url = {{http://doi.org/10.1039/d3sc06675d}},
volume = {{15}},
year = {{2024}},
}
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