4.8 Article

Palladium-Catalyzed Multicomponent Synthesis of Fully Substituted Alkylidene Furanones

Journal

ORGANIC LETTERS
Volume 22, Issue 17, Pages 7030-7033

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02578

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Funding

  1. EPFL (Switzerland)
  2. Swiss National Science Foundation (SNSF) [20020-155973]
  3. CONACYT (Mexico) [CVU 256937, 554166/290817]
  4. DAIP-UG

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In the presence of a catalytic amount of Pd(OAc)(2) and XantPhos, the three-component reaction of ynones, imines, and aryl iodides affords fully substituted alkylidene-furan-3(2H)-ones via a sequence of the Mannich reaction followed by chemo- and regioselective oxypalladation and reductive elimination. One carbon-oxygen and two carbon-carbon bonds are generated to afford the heterocycle in good to excellent yield.

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