One of the greatest challenges in C-H functionalization reactions is achieving high selectivity for the functionalization of a single C-H bond. Rhodium and ruthenium-catalyzed borylation of aliphatic C-H bonds is controlled by the steric properties of the substrate, leading to functionalization of terminal methyl groups; however, these catalysts have been unreactive towards secondary C-H bonds. Using knowledge gained from our studies on the iridium-catalyzed borylation of arenes, we have identified an Ir-catalyst for the borylation of secondary C-H bonds of cyclic ethers, with high selectively for functionalization at the position beta to oxygen. The same catalyst also mediates the borylation of cyclopropanes, with selectivity for functionalization of the methylene position over a terminal methyl group. The development and scope of these reactions will be presented.

Evolution of a catalyst for secondary C-H borylation

243rd National Meeting (2012)

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