Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime

Molecules. 2019 Nov 18;24(22):4177. doi: 10.3390/molecules24224177.

Abstract

We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaffolds found in FDA-approved pharmaceuticals.

Keywords: (Hetero)aryl halides; C-N Coupling; Copper catalyst; N-Nucleophiles; α-Benzoin oxime.

MeSH terms

  • Azoles / chemistry
  • Benzoin / analogs & derivatives*
  • Benzoin / chemistry
  • Carbon / chemistry
  • Catalysis
  • Copper / chemistry*
  • Halogens / chemistry*
  • Nitrogen / chemistry
  • Oximes / chemistry*
  • Piperidines / chemistry
  • Pyrrolidines / chemistry

Substances

  • Azoles
  • Halogens
  • Oximes
  • Piperidines
  • Pyrrolidines
  • alpha-benzoin oxime
  • Carbon
  • Copper
  • Benzoin
  • Nitrogen