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

Fingerprint

Palladium
Amines
Ligands
Substitution reactions
Molecules
X ray crystallography
X Ray Crystallography

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Palladium-Catalyzed Ligand-Free C-N Coupling Reactions : Selective Diheteroarylation of Amines with 2-Halobenzimidazoles. / Sang, Wei; Gavi, Ayao Jean; Yu, Bao Yi; Cheng, Hua; Yuan, Ye; Wu, Yuan; Lommens, Petra; Chen, Cheng; Verpoort, Francis.

In: Chemistry - An Asian Journal, Vol. 15, No. 1, 02.01.2020, p. 129-135.

Research output: Contribution to journalArticle

Sang, Wei ; Gavi, Ayao Jean ; Yu, Bao Yi ; Cheng, Hua ; Yuan, Ye ; Wu, Yuan ; Lommens, Petra ; Chen, Cheng ; Verpoort, Francis. / Palladium-Catalyzed Ligand-Free C-N Coupling Reactions : Selective Diheteroarylation of Amines with 2-Halobenzimidazoles. In: Chemistry - An Asian Journal. 2020 ; Vol. 15, No. 1. pp. 129-135.
@article{0a572381f5b040ecb3e420c66ebdfd6d,
title = "Palladium-Catalyzed Ligand-Free C-N Coupling Reactions: Selective Diheteroarylation of Amines with 2-Halobenzimidazoles",
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.",
keywords = "2-halobenzimidazoles, C-N coupling, di(hetero)arylation, ligand-free, palladium-catalyzed",
author = "Wei Sang and Gavi, {Ayao Jean} and Yu, {Bao Yi} and Hua Cheng and Ye Yuan and Yuan Wu and Petra Lommens and Cheng Chen and Francis Verpoort",
year = "2020",
month = "1",
day = "2",
doi = "10.1002/asia.201901465",
language = "English",
volume = "15",
pages = "129--135",
journal = "Chemistry - An Asian Journal",
issn = "1861-4728",
publisher = "John Wiley and Sons Ltd",
number = "1",

}

TY - JOUR

T1 - Palladium-Catalyzed Ligand-Free C-N Coupling Reactions

T2 - Selective Diheteroarylation of Amines with 2-Halobenzimidazoles

AU - Sang, Wei

AU - Gavi, Ayao Jean

AU - Yu, Bao Yi

AU - Cheng, Hua

AU - Yuan, Ye

AU - Wu, Yuan

AU - Lommens, Petra

AU - Chen, Cheng

AU - Verpoort, Francis

PY - 2020/1/2

Y1 - 2020/1/2

N2 - 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.

AB - 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.

KW - 2-halobenzimidazoles

KW - C-N coupling

KW - di(hetero)arylation

KW - ligand-free

KW - palladium-catalyzed

UR - http://www.scopus.com/inward/record.url?scp=85075746920&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85075746920&partnerID=8YFLogxK

U2 - 10.1002/asia.201901465

DO - 10.1002/asia.201901465

M3 - Article

C2 - 31762212

AN - SCOPUS:85075746920

VL - 15

SP - 129

EP - 135

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

SN - 1861-4728

IS - 1

ER -