Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with Diazodicarbonyls for Skeleton-Divergent Synthesis of Isocoumarins and Naphthalenes

Abstract

Diversity-oriented synthesis is tremendously useful for expanding the explorable chemical space but restricted by the limited available toolbox of skeleton-diversification chemistry. We report herein Rh(III)-catalyzed coupling of enaminones and diazodicarbonyls for skeleton-divergent synthesis of isocoumarins and naphthalenes. The diazodicarbonyl ring size and pH dependence of the skeleton-forming process demonstrates the achievement of both substrate- and reagent-controlled skeletal diversity generation in a single type of system. An intriguing C-C bond cleavage reactivity is critical for enabling facile synthetic access to isocoumarins.

Topics & Concepts