Pd/Pivalic Acid Mediated Direct Arylation of 2‐Pyrones and Related Heterocycles. Issue 16 (27th April 2015)

• Record Type: Journal Article
• Authors: Pardo, Leticia M.; Prendergast, Aisling M.; Nolan, Marie‐T.; Ó Muimhneacháin, Eoin; McGlacken, Gerard P.
• Is Part Of: European journal of organic chemistry. Issue 16(2015)
• Page Start: 3540
• Page End: 3550
• Publication Date: 2015-04-27
• Subjects: Synthetic methods -- Homogeneous catalysis -- Palladium -- C–C bond formation -- Arylation -- Oxygen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500262
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Direct arylation represents a favourable alternative to traditional cross‐coupling reactions and has found widespread use with simple aryls and robust heterocycles. Herein a direct arylation protocol has been optimised and applied to more delicate, privileged biological motifs. The intramolecular direct arylation of 2‐pyrones, 2‐coumarins, 2‐pyridones and 2‐quinolones occurs in very good to excellent yields using a Pd 0 source and pivalic acid as a crucial additive. Preliminary mechanistic investigations were also carried out. Abstract : Direct Arylation represents a favourable alternative to traditional cross‐coupling reactions. However there are limited reports on application to more delicate, privileged biological motifs. Herein the intramolecular Pd/PivOH promoted direct arylation of 2‐pyrones, 2‐coumarins, 2‐pyridones and 2‐quinolones is reported. One intermolecular example is included along with preliminary mechanistic investigations.