Amide directed iridium C(sp3)–H borylation catalysis with high N-methyl selectivity

Abstract A bidentate monoanionic ligand system was developed to enable iridium catalyzed C(sp3)–H activation borylation of N-methyl amides. Borylated amides were obtained in moderate to good isolated yields, and exclusive mono-borylation allowed the amide to be the limiting reagent. Selectivity for C(sp3)–H activation was demonstrated in the presence of sterically available C(sp3)–H bonds. Competitive kinetic isotope studies revealed a large primary isotope effect, implicating C–H activation as the rate limiting step.