Late-Stage Aromatic C–H Oxygenation

Synthetic methods
for oxidative aromatic C–O bond formation
are sparse, despite their demand in metabolite synthesis for drug
discovery and development. We report a novel methodology for late-stage
C–O bond formation of arenes. The reaction proceeds with excellent
functional group tolerance even for highly functionalized substrates.
The resulting aryl mesylates provide access to potential human metabolites
of pharmaceuticals, and may be used directly to install a C–F
bond to block metabolic hotspots. A charge-transfer interaction between
the reagent bis­(methane­sulfonyl) peroxide and the substrate
arenes may be relevant for the chemo­selective functionalization
of arenes over other functional groups.