Synthesis of C₂-Symmetric Benzimidazolium Salts and Their Application in Palladium-Catalyzed Enantioselective Intramolecular α-Arylation of Amides

Molecules. 2016 Jun 8;21(6):742. doi: 10.3390/molecules21060742.

Abstract

A series of C₂-symmetric chiral benzimidazolium salts, the precursor of N-heterocyclic carbene ligands, were designed and synthesized from 1,2-dibromobenzene. In situ prepared corresponding carbenes were tested in the asymmetric palladium-catalyzed intramolecular α-arylation of amides, affording chiral diarylmethanols with high yields and moderate enantioselectivities.

Keywords: N-heterocyclic carbene; Pd-catalyzed; asymmetric intramolecular α-arylation; benzimidazolium.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Anesthetics, Local / chemical synthesis
  • Anesthetics, Local / chemistry*
  • Bromobenzenes / chemical synthesis
  • Bromobenzenes / chemistry*
  • Catalysis
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Palladium / chemistry
  • Salts / chemistry
  • Stereoisomerism

Substances

  • Amides
  • Anesthetics, Local
  • Bromobenzenes
  • Indoles
  • Salts
  • carbene
  • 1,2-dibromobenzene
  • Palladium
  • Methane