Chemoselective C-H Hydroxylation and Borylation of N-Phenylbenzamides using BBr3

A novel metal-free chemoselective C-H hydroxylation and borylation of N-phenylbenzamides using BBr3 is described. The protocol generates the corresponding phenols and arylboronic esters in moderate to excellent yields under mild conditions with brilliant chemoselectivity. Additionally, this strategy can be realized in one pot, and several potential bioactive derivatives can be synthesized efficiently. Density functional theory calculations certify that the preferred pathway for this metal-free C-H hydroxylation process is the formation of a five-membered boracycle.