Chemoselective C–H Hydroxylation and Borylation of <i>N</i>-Phenylbenzamides using BBr<sub>3</sub>
Weiming Chen, Jiatao Xia, Jiuzhong Huang, Lianlian Zhou, Gaorong Wu
Abstract
A novel metal-free chemoselective C–H hydroxylation and borylation of N -phenylbenzamides using BBr 3 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.
Topics & Concepts
BorylationChemistryHydroxylationStereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryEnzymeAlkylArylCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis