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Copper-catalysed synthesis of α-alkylidene cyclic carbonates from propargylic alcohols and CO2

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We report a N-heterocyclic carbene copper(I) complex-catalysed formal cycloaddition between readily available propargylic alcohols and carbon dioxide at room temperature. By using the combination of a sterically demanding BPDPrCuCl complex (BPDPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-diazonine-2-ylid...

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Hauptverfasser: Cervantes Reyes, Alejandro (VerfasserIn) , Farshadfar, Kaveh (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Schaub, Thomas (VerfasserIn) , Ariafard, Alireza (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2021
In: Green chemistry
Year: 2021, Jahrgang: 23, Heft: 2, Pages: 889-897
ISSN:1463-9270
DOI:10.1039/D0GC03990J
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D0GC03990J
Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2021/gc/d0gc03990j
Volltext
Verfasserangaben:Alejandro Cervantes-Reyes, Kaveh Farshadfar, Matthias Rudolph, Frank Rominger, Thomas Schaub, Alireza Ariafard and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:We report a N-heterocyclic carbene copper(I) complex-catalysed formal cycloaddition between readily available propargylic alcohols and carbon dioxide at room temperature. By using the combination of a sterically demanding BPDPrCuCl complex (BPDPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-diazonine-2-ylidene) and CsF, as catalytic system, primary propargylic alcohols are efficiently converted to the corresponding α-alkylidene cyclic carbonates. Gram scale (up to 89% yield) and reusability experiments (74% global yield, turnover number value = 103) showcase the robustness of the catalytic system. This practically simple protocol also tolerates secondary and tertiary propargylic alcohols under CO2 at atmospheric pressure, enabling the direct synthesis of substituted and unsubstituted α-alkylidene cyclic carbonates at room temperature.
Beschreibung:First published 21 Dec 2020
Im Titel ist die Zahl "2" tiefgestellt
Gesehen am 08.09.2021
Beschreibung:Online Resource
ISSN:1463-9270
DOI:10.1039/D0GC03990J

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