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Late-Stage Aromatic C–H Oxygenation

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Börgel,  Jonas
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Tanwar,  Lalita
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Berger,  Florian
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ritter,  Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Börgel, J., Tanwar, L., Berger, F., & Ritter, T. (2018). Late-Stage Aromatic C–H Oxygenation. Journal of the American Chemical Society, 140(47), 16026-16031. doi:10.1021/jacs.8b09208.


Cite as: http://hdl.handle.net/21.11116/0000-0003-5757-A
Abstract
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.