Access to Some C5‐Cyclised 2‐Pyrones and 2‐Pyridones via Direct Arylation; Retention of Chloride as a Synthetic Handle. Issue 34 (13th September 2017)

• Record Type: Journal Article
• Authors: Prendergast, Aisling M.; Pardo, Leticia M.; Fairlamb, Ian J. S.; McGlacken, Gerard P.
• Is Part Of: European journal of inorganic chemistry. Issue 34(2017)
• Page Start: 5119
• Page End: 5124
• Publication Date: 2017-09-13
• Subjects: C‐H activation -- Cross‐coupling -- Heterocycles -- Palladium -- Synthetic methods; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201700980
• Languages: English
• ISSNs: 1434-1948

Abstract

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. Abstract : A direct arylation protocol was developed for the intramolecular coupling of 2‐pyrones and 2‐pyridones, allowing access to a previously unavailable class of products. A C–Cl bond was retained at C‐3 during the direct arylation process allowing further derivatisation (demonstrated by Suzuki–Miyaura coupling) at C‐3.