Modern approaches for the conversion of C-H bonds to C-B bonds involve transition metal catalysts that have various advantages over traditional methods by using cheap and abundant hydrocarbon starting materials, reducing toxic by-products and streamlining the synthesis of biologically important molecules. Metal-catalyzed C-H borylation reactions that produce organoboronic esters are mostly focused on the functionalization of sp2 C-H bonds of heteroarenes and aromatic hydrocarbons. However, in this work the functionalization of sp3 C-H bonds is being explored. Borylation involving sp3 C-H bonds have been shown by Sawamura and co-workers with solid silica supported phosphine ligands offering a directing strategy where a metal center can accept donor directing groups. While this ligand generates highly active borylation catalysts, it requires a lot of steps in the synthesis of the ligand. In this work, easily synthesized homogeneous bidentate monoanionic ligands were tested for the borylation of sp3 C-H bonds. Herein is reported borylation of sp3 C-H bonds of N-methyl amide groups using [Ir(OMe)(cod)]2 as a precatalyst and B2pin2 as a commercially available boron source. Following the borylation of amide as a directing group, amidine molecules are being investigated.
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