Ru(II)-Catalyzed Decarboxylative (4 + 2)-Annulation of Benzoic Acids and Benzamides with Propargyl Cyclic Carbonates.

ABSTRACT

Propargyl cyclic carbonates have emerged as versatile precursors in synthetic chemistry. However, their reactivity has so far been limited to transition metal-catalyzed substitution and cyclization reactions. Herein, we illustrate the successful employment of propargyl cyclic carbonates as coupling partners in Ru(II)-catalyzed C-H annulation of benzoic acids and benzamides. This approach allowed us to access a broad range of biologically relevant isocoumarin and isoquinolinone derivatives in good to excellent yields, utilizing bench-stable and easily accessible precursors. Preliminary mechanistic studies indicated that the C-H metalation step is both reversible and rate-determining in the reaction pathway. Furthermore, the utility of the developed methodology has been illustrated by scale-up and postfunctionalization experiments.