Nickel-Catalyzed Cross-Coupling of Aryl 2-Pyridyl Ethers with Organozinc Reagents: Removal of the Directing Group via Cleavage of the Carbon-Oxygen Bonds

Reaction of aryl 2-pyridyl ethers with arylzinc reagents under catalysis of NiCl2(PCy3)(2) affords aryl-aryl cross-coupling products via selective cleavage of C-Ar-OPy bonds. The reaction features a wide substrate range and good compatibility of functional groups. beta-H-free alkylzinc reagents are also applicable as the nucleophiles in the transformation, whereas beta-H-containing alkylzinc reagents lead to a mixture of cross-coupling and hydrogenation products.

Automated summary

The reaction of aryl 2-pyridyl ethers with arylzinc reagents catalyzed by NiCl2(PCy3)(2) can achieve aryl-aryl cross-coupling with a wide range of substrates and good functional group compatibility. It was found that beta-H-free alkylzinc reagents are more suitable as nucleophiles in this transformation.