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

Authors


  • We gratefully acknowledge the National Natural Sciences Foundation of China (21172031, 21272034 and 21372040), and the New Century Excellent Talents in Chinese University (NCET-11-0613) for financial support.

Abstract

The insertion of an aryne into a C[BOND]S bond can suppress the addition of an S nucleophile to the aryne in the presence of palladium. Catalyzed by Pd(OAc)2, a wide range of α-carbamoyl ketene dithioacetals readily react with arynes to selectively afford functionalized 2-quinolinones in high yields under neutral reaction conditions by a C[BOND]S 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.

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