Catalytic <i>Ortho</i>-Acetoxylation of Masked Benzyl Alcohols via an <i>Exo</i>-Directing Mode

Abstract

A Pd-catalyzed <i>ortho</i>-acetoxylation of masked benzyl alcohols to synthesize various 2-hydroxyalkylphenol derivatives is reported. The 2,6-dimethoxyl benzaldoxime proved to be an efficient <i>exo</i>-type directing group for arene (<i>sp</i>²) C–H functionalization. Two strategies were demonstrated to remove the directing group through N–O and C–O bond cleavages. A high catalyst turnover (>1000) was obtained to illustrate the practicality of this method