Nickel(II)-catalyzed addition reaction of arylboronic acids to isatins.

A Ni-catalyzed addition of arylboronic acids to isatins was first developed. The reaction, driven by Ni(acac) 2 and dppp as the phosphine ligand, gave 3-aryl-3-hydroxy-2-oxindoles in up to 97% yield. Scopes of benzyl-protected isatins and arylboronic acids were examined. Substituted phenylboronic acids along with fused-ring and heterocyclic boronic acids reacted with isatins smoothly. Preliminary asymmetric catalysis was investigated as well, showing moderate enantioselectivity. The mechanism was also described. [ABSTRACT FROM AUTHOR]