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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Site-selective aliphatic C-H oxidation is challenging, especially with labile aromatic groups.
  • Oxidizing strong methylene C-H bonds in the presence of aromatic functionalities is a key unsolved problem.
  • Chemoselective C-H oxidation is crucial for late-stage derivatization of pharmaceuticals and natural products.

Purpose of the Study:

  • To develop a catalyst system for selective oxidation of methylene C-H bonds adjacent to aromatic rings.
  • To achieve chemoselectivity in C-H oxidation, preserving sensitive aromatic functionalities.
  • To enable late-stage functionalization of drug scaffolds and natural products.

Main Methods:

  • Development of a manganese small-molecule catalyst, Mn(CF3-PDP).
  • Utilizing a synergistic effect between catalyst design and an acid additive.
  • Testing the catalyst on a diverse range of 50 aromatic compounds.

Main Results:

  • Achieved preparative remote methylene oxidation in 50 aromatic compounds with various functional groups (halogen, oxygen, heterocyclic, biaryl).
  • Demonstrated successful late-stage methylene oxidation on four drug scaffolds, including ethinylestradiol.
  • Showcased the catalyst's ability to outperform other C-H oxidants on specific scaffolds.
  • Facilitated rapid synthesis of a known metabolite (piragliatin) from an advanced intermediate.

Conclusions:

  • The Mn(CF3-PDP) catalyst system effectively achieves chemoselective methylene C-H oxidation.
  • This method provides a powerful tool for late-stage functionalization in drug discovery and development.
  • The catalyst's unique selectivity overcomes limitations of existing C-H oxidation methods.