Pardo, LM,Prendergast, AM,Nolan, MT,Muimhneachain, EO,McGlacken, GP

2015

June

European Journal of Organic Chemistry

Pd/Pivalic Acid Mediated Direct Arylation of 2-Pyrones and Related Heterocycles

Validated

Scopus: 18 ()

Synthetic methods Homogeneous catalysis Palladium C-C bond formation Arylation Oxygen heterocycles CATALYZED INTRAMOLECULAR ARYLATION PROTON-ABSTRACTION MECHANISM H BOND FUNCTIONALIZATION ONE-POT SYNTHESIS COUPLING REACTIONS REGIOSELECTIVE SYNTHESIS ARYL CHLORIDES PALLADIUM COUMARINS HALIDES

3540

3550

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.

10.1002/ejoc.201500262