4.7 Article

Catalytic Chemo- and Regioselective Coupling of 1,3-Dicarbonyls with N-Heterocyclic Nucleophiles

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 12, Pages 5162-5172

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00731

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Funding

  1. Lancaster University
  2. Royal Society of Chemistry

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The development of a decarboxylative palladium -catalyzed coupling of 1,3-dicarbonyl compounds with indole, pyrrole, imidazole, and pyrazole nucleophiles via an allylic linker under neutral conditions is disclosed. This process enables the installation of an all-carbon quaternary center and new C-C and C-N bonds in a single operation. Despite the weakly acidic nature of N-heterocycles, the reactions proceed with good efficiency and complete regio- and chemoselectivity.

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