Access to Some C5-Cyclised 2-Pyrones and 2-Pyridones via Direct Arylation; Retention of Chloride as a Synthetic Handle

Aisling M. Prendergast, Leticia M. Pardo, Ian J.S. Fairlamb, Gerard P. McGlacken*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The synthetic effort towards the functionalisation of C–H bonds on 2-pyrones and 2-pyridones has been enabled by the preferential reactivity of the C-3 position. Herein, we report a direct arylation protocol for the intramolecular coupling of 2-pyrones and 2-pyridones, allowing access to a previously unavailable class of C-5 cyclised products with an unstudied biological profile. A C–Cl bond was retained at C-3 during the direct arylation process allowing further derivatisation at C-3, using a Suzuki–Miyaura cross-coupling reaction.

Original languageEnglish
Pages (from-to)5119-5124
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number34
Early online date11 Sept 2017
Publication statusPublished - 13 Sept 2017

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© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.


  • C-H activation
  • Cross-coupling
  • Heterocycles
  • Palladium
  • Synthetic methods

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