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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MDPI AG
2025-02-01
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| Series: | Inorganics |
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| Online Access: | https://www.mdpi.com/2304-6740/13/2/59 |
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| author | Cody D. Amann Khushboo Eike B. Bauer |
| author_facet | Cody D. Amann Khushboo Eike B. Bauer |
| author_sort | Cody D. Amann |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-71bd9398a16b4516a5ca17f891cec00a |
| institution | DOAJ |
| issn | 2304-6740 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj-art-71bd9398a16b4516a5ca17f891cec00a2025-08-20T03:12:00ZengMDPI AGInorganics2304-67402025-02-011325910.3390/inorganics13020059Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization ReactionsCody D. Amann0Khushboo1Eike B. Bauer2Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USADepartment of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USADepartment of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USAA 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.https://www.mdpi.com/2304-6740/13/2/59diol cyclizationstrisubstituted tetrahydrofuransiron catalysisferrocenium catalysis |
| spellingShingle | Cody D. Amann Khushboo Eike B. Bauer Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions Inorganics diol cyclizations trisubstituted tetrahydrofurans iron catalysis ferrocenium catalysis |
| title | Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions |
| title_full | Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions |
| title_fullStr | Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions |
| title_full_unstemmed | Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions |
| title_short | Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions |
| title_sort | synthesis of 2 2 5 trisubstituted tetrahydrofurans by ferrocenium catalyzed dehydrative diol cyclization reactions |
| topic | diol cyclizations trisubstituted tetrahydrofurans iron catalysis ferrocenium catalysis |
| url | https://www.mdpi.com/2304-6740/13/2/59 |
| work_keys_str_mv | AT codydamann synthesisof225trisubstitutedtetrahydrofuransbyferroceniumcatalyzeddehydrativediolcyclizationreactions AT khushboo synthesisof225trisubstitutedtetrahydrofuransbyferroceniumcatalyzeddehydrativediolcyclizationreactions AT eikebbauer synthesisof225trisubstitutedtetrahydrofuransbyferroceniumcatalyzeddehydrativediolcyclizationreactions |