We report an intermolecular Ni-catalyzed reductive coupling of aryl iodides and isatins to form 3-hydroxyoxindoles. In contrast to common metal-mediated methods, sec-butanol is used as a mild stoichiometric reductant resulting in benign waste products. This formal 1,2-addition reaction is facilitated by a 1,5-diaza-3,7diphosphacyclooctane (P 2 N 2 ) ligand. Two Ni(0)−P 2 N 2 species are prepared and found to be catalytically active, supporting a mechanistic hypothesis that this reaction proceeds by a modified carbonyl-Heck-type pathway.