American Chemical Society
ol0c03701_si_001.pdf (6.73 MB)

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

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journal contribution
posted on 2020-12-22, 22:14 authored by Jing Jiang, Dandan Yuan, Congzhe Ma, Wanbin Song, Yaoyu Lin, Lihong Hu, Yinan Zhang
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 pre- and 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.