4.8 Article

Metal-ligand-Lewis acid multi-cooperative catalysis: a step forward in the Conia-ene reaction

Journal

CHEMICAL SCIENCE
Volume 12, Issue 1, Pages 435-441

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc05036a

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Funding

  1. Centre National de la Recherche Scientifique
  2. Universite de Toulouse
  3. European Commission [Au-MLC 841877]
  4. French government (MESRI, Ministere de l'Enseignement Superieur, de la Recherche et de l'Innovation)

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The new catalytic approach combines metal-ligand cooperation and Lewis acid activation to efficiently react with a variety of complex substrates, providing a new solution for the Conia-ene reaction.
An original multi-cooperative catalytic approach was developed by combining metal-ligand cooperation and Lewis acid activation. The [(SCS)Pd](2) complex featuring a non-innocent indenediide-based ligand was found to be a very efficient and versatile catalyst for the Conia-ene reaction, when associated with Mg(OTf)(2). The reaction operates at low catalytic loadings under mild conditions with HFIP as a co-solvent. It works with a variety of substrates, including those bearing internal alkynes. It displays complete 5-exo vs. 6-endo regio-selectivity. In addition, except for the highly congested Bu-t-substituent, the reaction occurs with high Z vs. E stereo-selectivity, making it synthetically useful and complementary to known catalysts.

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