Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions
A ferrocenium-catalyzed synthesis of trisubstituted tetrahydrofurans by dehydrative cyclization of diols is reported. Treatment of γ-phenyl-γ-butyrolactone or valerolactone with 2–3 equivalents of MeLi, <i>n</i>-BuLi, or PhLi yielded the corresponding substituted 1,4-butanediols in 41–86...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-02-01
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| Series: | Inorganics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2304-6740/13/2/59 |
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| Summary: | A ferrocenium-catalyzed synthesis of trisubstituted tetrahydrofurans by dehydrative cyclization of diols is reported. Treatment of γ-phenyl-γ-butyrolactone or valerolactone with 2–3 equivalents of MeLi, <i>n</i>-BuLi, or PhLi yielded the corresponding substituted 1,4-butanediols in 41–86% yields. Subsequent dehydrative cyclization of the diols under non-inert conditions using catalytic ferrocenium tetrafluoroborate (10 mol%) produced trisubstituted tetrahydrofurans in 72–83% yields after 48–72 h at 45–70 °C in CH<sub>2</sub>Cl<sub>2</sub>. This study demonstrates ferrocenium-catalyzed dehydrative cyclization for the first time, offering a convenient route to substituted tetrahydrofurans in two steps from commercial or easily accessible starting materials. |
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| ISSN: | 2304-6740 |