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Palladium‐Catalyzed Ligand‐Free C‐N Coupling Reactions: Selective Diheteroarylation of Amines with 2‐Halobenzimidazoles
Author(s) -
Sang Wei,
Gavi Ayao Jean,
Yu BaoYi,
Cheng Hua,
Yuan Ye,
Wu Yuan,
Lommens Petra,
Chen Cheng,
Verpoort Francis
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901465
Subject(s) - catalysis , palladium , ligand (biochemistry) , chemistry , selectivity , combinatorial chemistry , molecule , substitution (logic) , organic chemistry , computer science , biochemistry , receptor , programming language
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.