4.8 Article

Auto-Tandem Palladium Catalysis: From Isoxazole to 2-Azafluorenone

Journal

ORGANIC LETTERS
Volume 17, Issue 22, Pages 5578-5581

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02731

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Funding

  1. Queens College
  2. City University of New York

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An auto-tandem palladium catalysis from halogen-substituted isoxazoles and Michael acceptors is described. It involves two mechanistically distinct palladium-catalyzed reactions, a Heck reaction and a rearrangement, leading to 2-azafluorenones. It is the first example of palladium-catalyzed ring opening of isoxazoles and rearrangement of the beta-imino ketone ring-opening product.

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