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

• Verfasst von: Cervantes Reyes, Alejandro [VerfasserIn]
• Verfasst von: Farshadfar, Kaveh [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Schaub, Thomas [VerfasserIn]
• Verfasst von: Ariafard, Alireza [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Copper-catalysed synthesis of α-alkylidene cyclic carbonates from propargylic alcohols and CO2
• Verf.angabe: Alejandro Cervantes-Reyes, Kaveh Farshadfar, Matthias Rudolph, Frank Rominger, Thomas Schaub, Alireza Ariafard and A. Stephen K. Hashmi
• Jahr: 2021
• Umfang: 9 S.
• Fussnoten: First published 21 Dec 2020 ; Im Titel ist die Zahl "2" tiefgestellt ; Gesehen am 08.09.2021
• Titel Quelle: Enthalten in: Green chemistry
• Ort Quelle: Cambridge : RSC, 1999
• Jahr Quelle: 2021
• Band/Heft Quelle: 23(2021), 2, Seite 889-897
• ISSN Quelle: 1463-9270
• DOI: doi:10.1039/D0GC03990J
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1753324858

Abstract

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.