Palladium-Catalyzed Ligand-Free C-N Coupling Reactions: Selective Diheteroarylation of Amines with 2-Halobenzimidazoles

Wei Sang, Ayao Jean Gavi, Bao Yi Yu, Hua Cheng, Ye Yuan, Yuan Wu, Petra Lommens, Cheng Chen, Francis Verpoort

Research output: Contribution to journalArticle

Abstract

2-Aminobenzimidazoles are widely present in a number of bioactive molecules. Generally, the preparation of these molecules could be realized by the mono-substitution of 2-halobenzimidazoles with amines. However, rare examples were reported for the di-substituted products and the selectivity of mono- vs. di-substitution was relatively low. Considering the potential values of the di-substituted products, we accomplished the first selective diheteroarylation of amines with 2-halobenzimidazoles. Notably, this Pd-catalyzed transformation was realized under ligand-free conditions. Accordingly, numerous target products were efficiently produced from various aromatic or aliphatic amines and 2-halobenzimidazoles. It was worth noting that two representative products were further confirmed by X-ray crystallography. More significantly, this catalytic process could be applied to the synthesis and discovery of new bioactive compounds, which demonstrated the synthetic usefulness of this newly developed approach.

Original languageEnglish
Pages (from-to)129-135
Number of pages7
JournalChemistry - An Asian Journal
Volume15
Issue number1
DOIs
Publication statusPublished - 2 Jan 2020

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Keywords

  • 2-halobenzimidazoles
  • C-N coupling
  • di(hetero)arylation
  • ligand-free
  • palladium-catalyzed

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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