Strain‐Release‐Driven Electrochemical Skeletal Rearrangement of Non‐Biased Alkyl Cyclopropanes/Butanes
Abstract: Capitalizing the inherent strain energy within molecules, strain‐release‐driven reactions have been widely employed in organic synthesis. Small cycloalkanes like cyclopropanes and cyclobutanes, with their moderate ring strain, typically require dense functionalization to induce bias or distal activation of (hetero) aromatic rings via single‐electron oxidation for relieving the tension. In this study, we present a pioneering direct activation of alkyl cyclopropanes/butanes through electrochemical oxidation. This approach not only showcases the potential for ring‐opening of cyclopropane/butane under electrochemical conditions but also streamlines the synthesis of diverse oxazolines and oxazines. The applicability of our method is exemplified by its broad substrate scopes. Notably, the products derived from cyclobutanes undergo a formal ring contraction to cyclopropanes, introducing an intriguing aspect to our discoveries. These discoveries mark a significant advancement in strain‐release‐driven skeletal rearrangement reactions of moderately strained rings, offering sustainable and efficient synthetic pathways for future endeavours.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Strain‐Release‐Driven Electrochemical Skeletal Rearrangement of Non‐Biased Alkyl Cyclopropanes/Butanes ; day:30 ; month:10 ; year:2024 ; extent:10
Angewandte Chemie / International edition. International edition ; (30.10.2024) (gesamt 10)
- Creator
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Qi, Jing
Wang, Chu
Wang, Gan
O'Neill, Patrick
Reddy Dubbaka, Srinivas
Ting Ang, Hwee
Chen, Xuebo
Wu, Jie
- DOI
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10.1002/anie.202413723
- URN
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urn:nbn:de:101:1-2410301416544.528130046706
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:29 AM CEST
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Associated
- Qi, Jing
- Wang, Chu
- Wang, Gan
- O'Neill, Patrick
- Reddy Dubbaka, Srinivas
- Ting Ang, Hwee
- Chen, Xuebo
- Wu, Jie
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