4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 6, Pages 1697-1701

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712393

Keywords

annulation; cooperative catalysis; epoxides; norbornene; palladium

Funding

  1. University of Chicago
  2. 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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