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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Drug Discovery

Background:

  • Synthetic methods for oxidative aromatic C-O bond formation are limited.
  • Aromatic C-O bond formation is important for synthesizing drug metabolites.
  • Late-stage functionalization is key in drug discovery and development.

Purpose of the Study:

  • To develop a novel methodology for late-stage C-O bond formation of arenes.
  • To provide access to potential human metabolites of pharmaceuticals.
  • To enable blocking metabolic hotspots using C-F bonds.

Main Methods:

  • Utilized bis(methanesulfonyl) peroxide as a reagent.
  • Performed oxidative aromatic C-O bond formation on arenes.
  • Investigated functional group tolerance and chemoselectivity.

Main Results:

  • Achieved novel late-stage C-O bond formation of arenes.
  • Demonstrated excellent functional group tolerance for highly functionalized substrates.
  • Generated aryl mesylates as precursors to drug metabolites and for C-F bond installation.

Conclusions:

  • The developed method is valuable for synthesizing potential human metabolites.
  • The methodology allows for blocking metabolic hotspots by installing C-F bonds.
  • A charge-transfer interaction may explain the chemoselectivity of the reaction.