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Li Huang1, Qili Jiang1, Chunlan Song1

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This study introduces a novel photoredox/copper-catalyzed method for creating carbon-oxygen bonds to synthesize phosphates. This new technique offers improved selectivity and enables direct functionalization of complex molecules, overcoming limitations of traditional O-phosphorylation.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Traditional O-phosphorylation relies on O-P bond formation, limiting its scope to hydroxyl groups.
  • Existing methods lack selectivity, often requiring protection/deprotection steps for complex molecules.

Purpose of the Study:

  • To develop a novel method for phosphate synthesis via C-O bond formation.
  • To enable direct and selective late-stage functionalization of complex molecules with phosphates.

Main Methods:

  • Utilized a photoredox/copper-mediated catalytic system.
  • Employed arylthianthrenium salts to generate aryl radicals.
  • Captured aryl radicals with high-valent copper species to form C-O bonds with dialkyl phosphates.

Main Results:

  • Successfully constructed phosphates through challenging C-O bond formation.
  • Demonstrated a broad substrate scope, including complex drug molecules.
  • Achieved orthogonality with conventional O-phosphorylation methods.

Conclusions:

  • The developed method provides a versatile and selective route to phosphates via C-O bond formation.
  • Enables direct late-stage functionalization of complex molecules without protecting groups.
  • Offers a valuable alternative to traditional O-phosphorylation for challenging substrates.