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Direct Annulation between Aryl Iodides and Epoxides through Palladium/Norbornene Cooperative Catalysis
Author(s) -
Li Renhe,
Dong Guangbin
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712393
Subject(s) - annulation , norbornene , enantiopure drug , aryl , chemistry , palladium , epoxide , catalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis , alkyl , polymer , monomer
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.