-C-H functionalization of phenylethyl and benzylic alcohol derivatives Pd/NBE relay catalysis.

The transition metal-catalyzed -C-H functionalization of alcohols and their hydroxylamine derivatives remains underdeveloped. Herein, we report an efficient -C-H arylation of both phenylethyl and benzylic alcohols and their hydroxylamine derivatives using a readily removable oxime ether directing group. Using electronically activated 2-carbomethoxynorbornene as the transient mediator and 3-trifluoromethyl-2-pyridone as the enabling ligand, this reaction features a broad substrate scope and good functional group tolerance. More importantly, with this oxime-directed -C-H functionalization, this method provides a dual approach for efficient access to both -substituted alcohols and hydroxylamines using two sets of simple deprotection conditions. This protocol leads to the efficient synthesis of bioactive compounds possessing promising reactivities for the treatment of pulmonary fibrosis.