Tetrahedron
Tetrahedron
4 years ago

Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids

Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids
N-Arylation of (benz)imidazoles and amines with diarylborinic acids as cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric hindrance appeared to affect the copper-catalyzed N-arylation using the high-order arylboron reagent more significantly than the electronic factors, especially for low reactive anilines and aliphatic amines.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017310712

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