Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides

A highly efficient nickel/triarylphosphine catalyst system, Ni[P(4-MeOPh)(3)](2)Cl-2/2P(4-MeOPh)(3), has been developed for cross-coupling of diarylborinic acids with a wide range of aryl chlorides. A variety of unsymmetrical biaryl and heterobiaryl compounds with various functional groups and steric hindrance could be obtained in good to excellent yields using 0.5-2 mol % catalyst loadings in the presence of K3PO4 center dot 3H(2)O in toluene. The high atom economy of diarylborinic acids and cost-effectiveness of the nickel/phosphine catalyst system make the cross-coupling truly practical in the production of biaryl fine chemicals. Usefulness of the nickel/phosphine catalyzed cross-coupling of diarylborinic acids with aryl chlorides has been demonstrated in the development of a scalable and economical process for synthesis of 4'-methyl-2-cyanobiphenyl, Sartan biphenyl.