Iridium-Catalyzed, Substrate-Directed C–H Borylation Reactions of Benzylic Amines

Abstract

The iridium-catalyzed arene C–H borylation reaction of benzylic amines has been developed, which inverts the typical steric-controlled product distribution to provide <i>ortho</i>-substituted boronate esters. Picolylamine was found to be an ideal ligand to replace 4,4′-di-<i>tert</i>-butylbipyridine to induce the directing effect. Preliminary experiments are consistent with a mechanism involving dissociation of one amine of the hemilabile diamine ligand