Directing group assisted meta-hydroxylation by C–H activation

Abstract

<i>meta</i>-Hydroxylated cores are ubiquitous in natural products. Herein, we disclose the first template assisted <i>meta-</i>hydroxylation reaction. Experimental and <i>in silico</i> studies helped us to gain valuable mechanistic insights, including the role of the hexafluoroisopropanol (HFIP) solvent, during C-H hydroxylation. The reactive intermediates, prior to the C-H activation, have been detected by spectroscopic techniques. Additionally, the C-O bond formation has been extended to <i>meta</i>-acetoxylation. The preparation of a phase II quinone reductase activity inducer and a resveratrol precursor illustrated the synthetic significance of the present strategy.