Enaminones as Synthons for a Directed C-H Functionalization: RhIII-Catalyzed Synthesis of Naphthalenes

The use of enaminones as effective synthons for a directed C-H functionalization is reported. Proof-of-concept protocols have been developed for the Rh-III-catalyzed synthesis of naphthalenes, based on the coupling of enaminones with either alkynes or alpha-diazo-beta-ketoesters. Two inherently reactive functionalities (hydroxy and aldehyde groups) are integrated into the newly formed cyclic framework and a broad range of substituents are tolerated, rendering target products readily available for further elaboration.