Chiral Hemilabile P,N-Ligand-Assisted Gold Redox Catalysis for Enantioselective Alkene Aminoarylation

Chemistry. 2022 Jun 15;28(34):e202201018. doi: 10.1002/chem.202201018. Epub 2022 May 11.

Abstract

Enantioselective, intermolecular alkene arylamination was achieved through gold redox catalysis. Screening of ligands revealed chiral P,N ligands as the optimal choice, giving alkene aminoarylation with good yields (up to 80 %) and excellent stereoselectivity (up to 99 : 1 er). As the first example of enantioselective gold redox catalysis, this work confirmed the feasibility of applying a chiral ligand at the gold(I) stage, with the stereodetermining step (SDS) at the gold(III) intermediate, thus opening up a new way to conduct gold redox catalysis with stereochemistry control.

Keywords: alkenes; enantioselectivity; gold catalysis; hemilabile ligand; redox chemistry.

MeSH terms

  • Alkenes* / chemistry
  • Catalysis
  • Gold* / chemistry
  • Ligands
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alkenes
  • Ligands
  • Gold