Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 6, Pages 1697-1701Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712393
Keywords
annulation; cooperative catalysis; epoxides; norbornene; palladium
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Funding
- University of Chicago
- Eli Lilly
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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.
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