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

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JournalEuropean Journal of Organic Chemistry
DateAccepted/In press - 4 Aug 2017
DateE-pub ahead of print - 11 Sep 2017
DatePublished (current) - 13 Sep 2017
Issue number34
Volume2017
Number of pages6
Pages (from-to)5119-5124
Early online date11/09/17
Original languageEnglish

Abstract

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.

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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.

    Research areas

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

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