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Synthesis
DOI: 10.1055/a-2714-9637
DOI: 10.1055/a-2714-9637
Paper
C–F Bond Functionalization with Organolithium Compounds
Autoren
We gratefully acknowledge financial support from the US National Institutes of Health (GM106260).
Abstract
Cross-coupling of alkyl fluorides and organolithium compounds is achieved by liquid-assisted stirring and mild heating without the need for expensive catalysts or additives. The reaction proceeds with a variety of primary, secondary, and tertiary fluorides; several functional groups, including alkyl halides, ether, amide, and heteroaryl groups, are tolerated; and both aryl and alkyllithium compounds can be used. Mechanistic studies indicate that the reaction involves heterolytic C–F bond activation and proceeds either via generation of short-lived carbocation intermediates or through a concerted pathway, which probably predominates with primary substrates, while the formation of thermodynamically stable lithium fluoride is the driving force.
Keywords
Alkyl fluorides - Cross-coupling - Organolithium reagents - C–F bond functionalization - Liquid-assisted mixingPublikationsverlauf
Eingereicht: 20. August 2025
Angenommen nach Revision: 01. Oktober 2025
Accepted Manuscript online:
01. Oktober 2025
Artikel online veröffentlicht:
27. Oktober 2025
© 2025. Thieme. All rights reserved.
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