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

Cervantes-Reyes, A, Farshadfar, K, Rudolph, M, Rominger, F, Schaub, T, Ariafard, A ORCID: 0000-0003-2383-6380 and Hashmi, ASK 2021 , 'Copper-catalysed synthesis of alpha-alkylidene cyclic carbonates from propargylic alcohols and CO2' , Green Chemistry, vol. 23, no. 2 , pp. 889-897 , doi:

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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-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 Type: Article
Authors/Creators:Cervantes-Reyes, A and Farshadfar, K and Rudolph, M and Rominger, F and Schaub, T and Ariafard, A and Hashmi, ASK
Keywords: copper catalysis, CO2 activation, DFT calculations
Journal or Publication Title: Green Chemistry
Publisher: Royal Soc Chemistry
ISSN: 1463-9262
DOI / ID Number:
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This journal is © The Royal Society of Chemistry 2021

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