Palladium-Catalyzed C-S Activation/Aryne Insertion/Coupling Sequence: Synthesis of Functionalized 2-Quinolinones

The insertion of an aryne into a CS bond can suppress the addition of an Snucleophile to the aryne in the presence of palladium. Catalyzed by Pd(OAc)(2), a wide range of -carbamoyl ketene dithioacetals readily react with arynes to selectively afford functionalized 2-quinolinones in high yields under neutral reaction conditions by a CS activation/aryne insertion/intramolecular coupling sequence. The attractive feature of the new strategy also lies in the versatile transformations of the alkythio-substituted quinolinone products.