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Copper-catalysed synthesis of alpha-alkylidene cyclic carbonates from propargylic alcohols and CO2
Citation
Cervantes-Reyes, A and Farshadfar, K and Rudolph, M and Rominger, F and Schaub, T and Ariafard, A and Hashmi, ASK, Copper-catalysed synthesis of alpha-alkylidene cyclic carbonates from propargylic alcohols and CO2, Green Chemistry, 23, (2) pp. 889-897. ISSN 1463-9262 (2021) [Refereed Article]
Copyright Statement
This journal is © The Royal Society of Chemistry 2021
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.
Item Details
Item Type: | Refereed Article |
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Keywords: | copper catalysis, CO2 activation, DFT calculations |
Research Division: | Chemical Sciences |
Research Group: | Physical chemistry |
Research Field: | Catalysis and mechanisms of reactions |
Objective Division: | Expanding Knowledge |
Objective Group: | Expanding knowledge |
Objective Field: | Expanding knowledge in the chemical sciences |
UTAS Author: | Ariafard, A (Associate Professor Alireza Ariafard) |
ID Code: | 150048 |
Year Published: | 2021 |
Funding Support: | Australian Research Council (DP180100904) |
Web of Science® Times Cited: | 8 |
Deposited By: | College Office - CoSE |
Deposited On: | 2022-05-16 |
Last Modified: | 2022-07-22 |
Downloads: | 0 |
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