Organic & Biomolecular Chemistry 2012-04-07

A new access to 3-substituted-1(2H)-isoquinolone by tandem palladium-catalyzed intramolecular aminocarbonylation annulation.

Antoine Dieudonné-Vatran, Michel Azoulay, Jean-Claude Florent

Index: Org. Biomol. Chem. 13th ed., 10 , 2683-2691, (2012)

Full Text: HTML

Abstract

An original tribromide derivative based, palladium-catalyzed synthesis of 3-substituted-1(2H)-isoquinolone is described based on a regioselective Suzuki-Miyaura C-C coupling on o-halo-(2,2-dihalovinyl)-benzene followed by a palladium catalyzed amination-carbonylation-cyclization reaction. This sequence efficiently proceeds to build up isoquinolone in fair to good yields over a one-pot 3-bond synthesis reaction.