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The development of an operationally simple C–H oxidation protocol using an acid-stable, bis(bipyridine)Ru catalyst is described. Electronic differences remote to the site of C–H functionalization are found to affect product selectivity. Site-selectivity is further influenced by the choice of reaction solvent, with highest levels of 2° methylene oxidation favored in aqueous dichloroacetic acid. A statistical model is detailed that correlates product selectivity outcomes with computational parameters describing the relative “electron-richness” of C–H bonds.
Griffin et al. (Mon,) studied this question.