Dearomative Ring Expansion of Polycyclic Arenes
Abstract: Benzocycloheptenes constitute a common structural motif embedded in many natural products and biologically active compounds. Herein, we report their concise preparation from non‐activated polycyclic arenes using a two‐step sequence involving dearomative [4+2]‐cycloaddition with arenophile in combination with palladium‐catalyzed cyclopropanation, followed by cycloreversion‐initiated ring expansion. The described strategy provides a working alternative to the Buchner reaction, which is limited to monocyclic arenes. Overall, this methylene‐insertion molecular editing approach enables rapid and direct conversion of simple (hetero) arenes into a range of substituted (aza) benzocycloheptatrienes, which can undergo a myriad of downstream functionalizations.
- 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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Dearomative Ring Expansion of Polycyclic Arenes ; day:26 ; month:07 ; year:2022 ; extent:1
Angewandte Chemie ; (26.07.2022) (gesamt 1)
- Creator
- DOI
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10.1002/ange.202208014
- URN
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urn:nbn:de:101:1-2022072615103326067733
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
- 15.08.2025, 7:36 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Piacentini, Paolo
- Bingham, Tanner W.
- Sarlah, David
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Dearomative Ring Expansion of Polycyclic Arenes
Arene Ring Expansion by Ruthenium η 6 ‐Arene Complexes
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Electronic interactions between polycyclic arenes in cyclophanes
Polycyclic arenes and heteroarenes : synthesis, properties, and applications
Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization
Polycyclic and oligocyclic phosphorus-nitrogen ring systems
Introducing Reduction to Polycyclic Group Rings - A Comparison of Methods
Ring expansion and ring opening of heteroaromatic nitrenes
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