Palladium-Catalyzed Regiospecific peri- and ortho-C-H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups

An efficient divergent approach of Pd-catalyzed C-H oxygenation of polyaromatic rings is described. Reversible directing groups enable regiospecific peri- and ortho-oxygenation to readily access a wide array of polyaromatic phenols without preand postmanipulation of directing groups. The systematic mechanistic investigation, including deuterium-labeling experiments, palladacycle trapping, and DFT calculations, reveals that the tunable ligand-assisted C-H bond cleavage played a crucial role during the reaction process.

Automated summary

An efficient divergent approach of Pd-catalyzed C-H oxygenation of polyaromatic rings is described, utilizing reversible directing groups to achieve regiospecific oxygenation. Mechanistic investigation, including deuterium-labeling experiments and DFT calculations, reveals the crucial role of tunable ligand-assisted C-H bond cleavage during the reaction process.