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 language | English |
|---|---|
| Pages (from-to) | 129-135 |
| Number of pages | 7 |
| Journal | Chemistry - An Asian Journal |
| Volume | 15 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 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
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 journal › Article
}
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 -