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Copper-catalysed synthesis of alpha-alkylidene cyclic carbonates from propargylic alcohols and CO2
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.
Funding
Australian Research Council
University of Wollongong
History
Publication title
Green ChemistryVolume
23Pagination
889-897ISSN
1463-9262Department/School
College Office - College of Sciences and EngineeringPublisher
Royal Soc ChemistryPlace of publication
Thomas Graham House, Science Park, Milton Rd, Cambridge, England, Cambs, Cb4 0WfRights statement
This journal is © The Royal Society of Chemistry 2021Repository Status
- Restricted