4.7 Article

Direct Access to 2,3-Disubstituted Amido-Indenones through Annulation of 2-Iodobenzaldehydes with Ynamides

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 24, Pages 16860-16866

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02054

Keywords

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Funding

  1. CNRS
  2. University of Strasbourg
  3. French National Agency of Research (ANR)
  4. French Ministry of Higher Education, Research, and Innovation
  5. [ANR-CE07-19-0016]

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This paper reports a palladium-catalyzed annulation reaction that can synthesize polysubstituted amino-indenones, with different regioselectivity observed between different ynamides.
In this paper we report the annulation reaction between 2-iodobenzaldehyde derivatives and various ynamides. This palladium-catalyzed reaction leads to rare polysubstituted amino-indenones in good yields with a regioselectivity up to complete. Remarkably, a regiodivergent selectivity has been identified between aryl and alkyl or silyl ynamides, with the first leading mainly to 2-amido-indenones and the second to 3-amido-indenones.

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