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Synlett
DOI: 10.1055/a-2640-2610
DOI: 10.1055/a-2640-2610
letter
Thiolate-Initiated Metal-Free Synthesis of Cyclopentenones via a Halogen-Stabilized Vinyl Carbanion
Supported by: Universität Duisburg-Essen
A metal-free synthesis of cyclopentenones is described. The mechanism proceeds via a halogen-stabilized carbanion generated by the nucleophilic attack of a thiolate on a haloalkyne moiety. The sp2-hybridized carbanion undergoes cyclization to an embedded ester carbonyl, yielding the cyclopentenone. The reaction exhibits a broad tolerance toward functional groups and proceeds under mild conditions.
Publication History
Received: 13 May 2025
Accepted after revision: 19 June 2025
Accepted Manuscript online:
20 June 2025
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