Direct Annulation between Aryl Iodides and Epoxides through Palladium/Norbornene Cooperative Catalysis

Abstract

Herein we report a direct annulation between aryl iodides and epoxides through palladium/norbornene (Pd/NBE) cooperative catalysis. An iso-propyl ester substituted NBE was found to be most efficient to suppress the formation of multiple-NBE-insertion byproducts and affords the desired 2,3-dihydrobenzofuran derivatives in 44-99 % yields. The reaction is scalable and tolerates a range of functional groups. Asymmetric synthesis is realized using an enantiopure epoxide. Application of this method into a concise synthesis of insecticide fufenozide is demonstrated.