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An organocatalytic route to endo-vinylene carbonates from carbon dioxide-based exo-vinylene carbonates

An organocatalytic route has been developed for the isomerization of exo-vinylene carbonates (exo-VCs) to endo-vinylene carbonates (endo-VCs). The exo-VC starting material can easily be obtained from propargylic alcohols via cyclization with carbon dioxide. In this study, these exo-VCs are shown to...

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Hauptverfasser: Qiao, Chang (VerfasserIn) , Engel, Philipp D. (VerfasserIn) , Ziegenhagen, Levi A. (VerfasserIn) , Rominger, Frank (VerfasserIn) , Schäfer, Ansgar (VerfasserIn) , Deglmann, Peter (VerfasserIn) , Rudolf, Peter (VerfasserIn) , Comba, Peter (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn) , Schaub, Thomas (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: January 30, 2024
In: Advanced synthesis & catalysis
Year: 2024, Jahrgang: 366, Heft: 2, Pages: 291-298
ISSN:1615-4169
DOI:10.1002/adsc.202301374
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/adsc.202301374
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202301374
Volltext
Verfasserangaben:Chang Qiao, Philipp D. Engel, Levi A. Ziegenhagen, Frank Rominger, Ansgar Schäfer, Peter Deglmann, Peter Rudolf, Peter Comba, A. Stephen K. Hashmi, and Thomas Schaub
Beschreibung
Zusammenfassung:An organocatalytic route has been developed for the isomerization of exo-vinylene carbonates (exo-VCs) to endo-vinylene carbonates (endo-VCs). The exo-VC starting material can easily be obtained from propargylic alcohols via cyclization with carbon dioxide. In this study, these exo-VCs are shown to isomerize to the thermodynamically more stable endo-VCs in the presence of an N-heterocyclic base and phenol. Density functional theory (DFT) studies were conducted to elucidate the mechanism, tackling difficulties of the description of charge separation steps. This isomerization process delivers an ample diversity of endo-VCs in good to excellent yields and chemoselectivities under mild reaction conditions.
Beschreibung:Veröffentlicht: 05 December 2023. Version des Artikels : December 15, 2023
Gesehen am 26.02.2024
Beschreibung:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.202301374

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