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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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Main Authors: Qiao, Chang (Author) , Engel, Philipp D. (Author) , Ziegenhagen, Levi A. (Author) , Rominger, Frank (Author) , Schäfer, Ansgar (Author) , Deglmann, Peter (Author) , Rudolf, Peter (Author) , Comba, Peter (Author) , Hashmi, A. Stephen K. (Author) , Schaub, Thomas (Author)
Format: Article (Journal)
Language:English
Published: January 30, 2024
In: Advanced synthesis & catalysis
Year: 2024, Volume: 366, Issue: 2, Pages: 291-298
ISSN:1615-4169
DOI:10.1002/adsc.202301374
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/adsc.202301374
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202301374
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Author Notes: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
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Summary: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.
Item Description:Veröffentlicht: 05 December 2023. Version des Artikels : December 15, 2023
Gesehen am 26.02.2024
Physical Description:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.202301374

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